{"id":24938,"date":"2020-11-05T18:36:55","date_gmt":"2020-11-06T01:36:55","guid":{"rendered":"https:\/\/hepatochem.com\/photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions\/"},"modified":"2020-11-05T18:36:55","modified_gmt":"2020-11-06T01:36:55","slug":"photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions","status":"publish","type":"post","link":"https:\/\/hepatochem.com\/fr\/photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions\/","title":{"rendered":"Photochemistry 101, Part III: Setting Up Your Initial Photochemistry Reactions"},"content":{"rendered":"<p>[et_pb_section fb_built=\u00a0\u00bb1&Prime; _builder_version=\u00a0\u00bb4.27.2&Prime; hover_enabled=\u00a0\u00bb0&Prime; global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb custom_margin=\u00a0\u00bb0px||||false|false\u00a0\u00bb custom_padding=\u00a0\u00bb0px||||false|false\u00a0\u00bb sticky_enabled=\u00a0\u00bb0&Prime;][et_pb_row _builder_version=\u00a0\u00bb4.27.2&Prime; background_size=\u00a0\u00bbinitial\u00a0\u00bb background_position=\u00a0\u00bbtop_left\u00a0\u00bb background_repeat=\u00a0\u00bbrepeat\u00a0\u00bb hover_enabled=\u00a0\u00bb0&Prime; global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb custom_margin=\u00a0\u00bb0px||||false|false\u00a0\u00bb custom_padding=\u00a0\u00bb0px||||false|false\u00a0\u00bb sticky_enabled=\u00a0\u00bb0&Prime; width=\u00a0\u00bb100%\u00a0\u00bb][et_pb_column type=\u00a0\u00bb4_4&Prime; _builder_version=\u00a0\u00bb4.16&Prime; custom_padding=\u00a0\u00bb|||\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb custom_padding__hover=\u00a0\u00bb|||\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][et_pb_text _builder_version=\u00a0\u00bb4.27.2&Prime; background_size=\u00a0\u00bbinitial\u00a0\u00bb background_position=\u00a0\u00bbtop_left\u00a0\u00bb background_repeat=\u00a0\u00bbrepeat\u00a0\u00bb hover_enabled=\u00a0\u00bb0&Prime; global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb custom_margin=\u00a0\u00bb0px||||false|false\u00a0\u00bb custom_padding=\u00a0\u00bb0px||||false|false\u00a0\u00bb sticky_enabled=\u00a0\u00bb0&Prime;]<\/p>\n<h2>Setting Up Your Initial Photochemistry Reactions<\/h2>\n<p><span style=\"font-weight: 400;\"><em>This is the third and final part of a three part series designed to help you get started by understanding light sources in photochemistry. Missed the start of the series where we cover the basics and core principles? No worries, <a href=\"https:\/\/hepatochem.com\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/\">you can read it here<\/a>&#8230;<\/em><\/span><\/p>\n<p><span style=\"font-weight: 400;\">Visible light photoredox catalysis uses the excited states of metal complexes and organic dyes to perform energy transfer and single-electron transfer (SET) processes for an ever-increasing number of useful synthetic transformations. As should be apparent from reading <strong>Part 1<\/strong> (<a href=\"https:\/\/hepatochem.com\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/\">\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/<\/a>) and <strong>Part 2<\/strong> (<a href=\"https:\/\/hepatochem.com\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\/\">\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\/<\/a>), we think photochemistry is pretty cool. But is it useful? The possibilities of where to start first can seem daunting. A standard reaction setup is imperative for reproducible chemistry from lab to lab enabling a low barrier to entry for the field. As you just read, step one to standardizing reactions is a better understanding of the light source. The second step is the reactor. Let&rsquo;s do a quick review before we start providing details on your <\/span>initial photochemistry reactions.<\/p>\n<p><span style=\"font-weight: 400;\">First, it is a simple concept at first but needs to be stated. <strong>The only light that is useful to running your reaction is the light that actually makes its way into the flask<\/strong>. The bright blue light shining on the back of your hood isn&rsquo;t doing anything. For this reason, we have developed a series of photoreactors to maximize light intensity, control temperature and standardize reaction conditions that are currently in use in both industrial and academic settings (Ref 20). For use with a standardized setup, (the <a href=\"\/photoreactors-leds-accessories-old\/photoredox-box\/\">EvoluChem Photoredox Box<\/a>), we have selected and adapted four reactions from the literature as a convenient starting point for those new to photochemistry. Each reaction has been tested and validated in our equipment. Each is available as a part of bundle including photoreactor, sample holders, LED&rsquo;s and premixed reactions to run test reaction, as well as three substrate combinations of your choice (see <a href=\"\/photoreactors-leds-accessories\/photochemistry-starter-bundle\/\">https:\/\/hepatochem.com\/photoreactors-leds-accessories\/photochemistry-starter-bundle\/<\/a>).<\/span><\/p>\n<h2>Experimental Details<\/h2>\n<p><span style=\"font-weight: 400;\">Each reaction is performed in the Evoluchem PhotoRedOx box, equipped with either an 18W 450 nm or 365 nm <a href=\"#\">Evoluchem LED<\/a>. Reactions are performed in 4 mL vials equipped with a Teflon septa cap containing pre-weighed photocatalyst, co-catalyst base and reagents. Substrate solutions are added via syringe and the reaction is sparged with a N2 line via needle for 5 minutes prior to turning on the LED&rsquo;s. The reactor is equipped with a fan that holds the reaction temperature stable at ~30 \u00b0C. Reactions are run for 18-24 hr. Product analysis is performed by LC-MS.<\/span><\/p>\n<h2>Initial Photochemistry Reactions:C-C cross-coupling with amino acid decarboxylation<\/h2>\n<p><em><span style=\"font-weight: 400;\">Adapted from Ref 14<br \/><\/span><\/em><span style=\"font-weight: 400;\">The first reaction that we want to highlight is an Iridium\/nickel catalyzed carbon-carbon bond formation as described by MacMillan and coworkers (Ref 14). This approach uses a commercially available iridium catalyst (Ir[dF(CF<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">)ppy]<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">(dtbbpy)PF<\/span><span style=\"font-weight: 400;\"><sub>6<\/sub> <\/span><span style=\"font-weight: 400;\">(structure in <strong>Figure 2<\/strong>) with a CFL bulb. The photoredox cycle activates a nickel catalyzed organometallic cycle for the coupling of \u03b1-carboxyl sp<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">-carbons with aryl halides. The nickel catalyst is formed <\/span><i><span style=\"font-weight: 400;\">in situ <\/span><\/i><span style=\"font-weight: 400;\">between NiCl<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub> <\/span><span style=\"font-weight: 400;\">with dtbbpy as a ligand. The reaction requires a base (Cs<\/span><span style=\"font-weight: 400;\">2<\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen. The reaction demonstrated coupling for a wide range of carboxylic acids with aryl bromides, iodides and select chlorides. The test reaction we have selected is the coupling of N-Boc-Valine and 4-bromoacetophenone which we have adapted from the reported procedure to use 450 nm LED instead of the CFL (<strong>Figure 8<\/strong>).<\/span><\/p>\n<div id=\"attachment_8563\" style=\"width: 700px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8563\" class=\"wp-image-8563 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure8.png\" alt=\"initial photochemistry reactions: Carbon-carbon formation between sp3 carbons and aryl halides\" width=\"690\" height=\"186\" srcset=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure8.png 690w, https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure8-480x129.png 480w\" sizes=\"(min-width: 0px) and (max-width: 480px) 480px, (min-width: 481px) 690px, 100vw\" \/><p id=\"caption-attachment-8563\" class=\"wp-caption-text\"><strong>Figure 8:<\/strong> Carbon-carbon formation between sp3 carbons and aryl halides (adapted from Ref 14)<\/p><\/div>\n<h2>Initial Photochemistry Reactions:C-O bond formation<\/h2>\n<p><span style=\"font-weight: 400;\">The second reaction that we have selected is also by MacMillan and coworkers using Ir\/Ni catalysis, however this time for C-O bond formation<\/span> <span style=\"font-weight: 400;\">(Ref 21). This reaction also uses (Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(dtbbpy)PF<sub>6<\/sub><\/span><span style=\"font-weight: 400;\">, NiCl<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub> <\/span><span style=\"font-weight: 400;\">and dtbbpy as a ligand. This reaction requires quinuclidine as an electron donor\/acceptor and an additional base. The reaction uses primary and secondary alcohol for C-O bond formation with aryl bromides. The reaction requires a base (K<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen. Nickel itself is unable to perform C-O couplings without the use of high temperatures due to the stability of nickel-alkoxide complexes. The photoredox cycle using a 450 nm LED and the iridium catalyst can activate this cycle at room temperature for a wide variety of alcohols and aryl bromides. The test reaction that we have selected is the coupling of cyclohexanol and 4-bromoacetophenone with 450 nm (<strong>Figure 9<\/strong>).<\/span><\/p>\n<div id=\"attachment_8564\" style=\"width: 727px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8564\" class=\"wp-image-8564 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure9.png\" alt=\"initial photochemistry reactions: C-O bond formation\" width=\"717\" height=\"225\" srcset=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure9.png 717w, https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure9-480x151.png 480w\" sizes=\"(min-width: 0px) and (max-width: 480px) 480px, (min-width: 481px) 717px, 100vw\" \/><p id=\"caption-attachment-8564\" class=\"wp-caption-text\"><strong>Figure 9:<\/strong> C-O bond formation (Adapted from Ref 21)<\/p><\/div>\n<h2><\/h2>\n<h2>Initial Photochemistry Reactions:C-C Cross coupling with BF<sub>3<\/sub>K reagents<\/h2>\n<p><span style=\"font-weight: 400;\">The third reaction that we want to highlight is also a C-C bond formation, however this time using an alkyl BF<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">K reagent as the coupling partner. Molander and coworkers have performed a substantial amount of work using BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> reagents for photoredox catalyzed transformations. The reaction we are focusing on is the Iridium\/nickel catalyzed cross coupling of aryl bromides with secondary alkyl BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\">reagents (<strong>Ref 22<\/strong>). BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> reagents are easy to handle, bench stable solid reagents useful for many cross-coupling reactions. This reaction works extremely well for a wide range of alkyl-BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\">with aryl bromides and can very quickly be used to generate a large series of analogues. The reaction requires a base (Cs<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen. The test reaction we have selected uses cyclohexyl-BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> and 4-bromoacetophenone (Figure 10). We have modified the reaction condition to use Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(dtbbpy)PF<sub>6<\/sub><\/span> <span style=\"font-weight: 400;\">instead of Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(bpy)PF<sub>6<\/sub><\/span><span style=\"font-weight: 400;\">(slightly different ligand), lowered the catalyst loading and use 450 nm LEDs instead of CFL.<\/span><\/p>\n<div id=\"attachment_8565\" style=\"width: 759px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8565\" class=\"wp-image-8565 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure10.png\" alt=\"initial photochemistry reactions: C-C cross-coupling with BF3K reagents \" width=\"749\" height=\"224\" srcset=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure10.png 749w, https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure10-480x144.png 480w\" sizes=\"(min-width: 0px) and (max-width: 480px) 480px, (min-width: 481px) 749px, 100vw\" \/><p id=\"caption-attachment-8565\" class=\"wp-caption-text\"><strong>Figure 10:<\/strong> C-C cross-coupling with BF3K reagents (adapted from Ref 22)<\/p><\/div>\n<h2>Initial Photochemistry Reactions:C\u00e2\u02c6\u2019N Cross-Coupling via Photoexcitation of Nickel\u00e2\u02c6\u2019Amine Complexes<\/h2>\n<p><span style=\"font-weight: 400;\">The final reaction we have selected is a carbon-nitrogen cross coupling reaction as described by Miyake and coworkers (<strong>Ref 23<\/strong>). This is the first reaction that we have selected that does not include an iridium catalyst or 450 nm LED. Here, the inexpensive NiBr<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span> <span style=\"font-weight: 400;\">salt forms a photoactive complex with primary and secondary amines that can be excited by 365 nm LED&rsquo;s to give C-N bond formation products using aryl bromides. When excess amine is used, the addition of quinuclidine is not required. The reaction should be sparged with nitrogen to remove oxygen. Of note, this reaction is run at higher concentration than the previously selected reactions and the Ni-amine complex could be described as the photocatalyst for the reaction. We have selected the coupling of morpholine with 4-bromoacetophenone without quinuclidine.<\/span><\/p>\n<div id=\"attachment_8566\" style=\"width: 752px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8566\" class=\"wp-image-8566 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure11.png\" alt=\"initial photochemistry reactions: C-N Cross-coupling reaction\" width=\"742\" height=\"208\" srcset=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure11.png 742w, https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure11-480x135.png 480w\" sizes=\"(min-width: 0px) and (max-width: 480px) 480px, (min-width: 481px) 742px, 100vw\" \/><p id=\"caption-attachment-8566\" class=\"wp-caption-text\"><strong>Figure 11:<\/strong> C-N Cross-coupling reaction (Ref 23)<\/p><\/div>\n<p>&nbsp;<\/p>\n<p>We hope you have enjoyed this series on Photochemistry 101 and invite you to email us (<a href=\"mailto:info@hepatochem.com\">info@hepatochem.com<\/a>) or follow us on Twitter (<a href=\"https:\/\/twitter.com\/EvoluChem\">@EvoluChem<\/a>) to suggest more content and subject areas you would like us to cover. If you have any questions about the experiments above, or just find yourself stuck and looking for a good listener&#8230; drop us a line! Check out our starter bundle and give photoredox catalysis a try!<\/p>\n<p><em><span style=\"font-weight: 400;\">You just read the third and final part of a three part series designed to help you get started in photochemistry. Below are links to all three parts of the series. Any questions? Send them to <a href=\"mailto:info@hepatochem.com\">info@hepatochem.com<\/a>, we&rsquo;d love to hear from you!<br \/>Here&rsquo;s the entire series:<\/span><\/em><\/p>\n<p><a href=\"https:\/\/hepatochem.com\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/\"><strong>Photochemistry 101, Part I: Everything You Need To Know To Get Started<\/strong><\/a><\/p>\n<p><a href=\"https:\/\/hepatochem.com\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\/\"><strong>Photochemistry 101, Part II: Understanding and Measuring Light Sources<\/strong><\/a><\/p>\n<p><a href=\"https:\/\/hepatochem.com\/fr\/photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions\/\"><strong><span style=\"font-weight: 400;\"><strong>Photochemistry 101, Part III: Setting Up Your Initial Photochemistry Reactions<\/strong><\/span><\/strong><\/a><\/p>\n<p>&nbsp;<\/p>\n<p><b>References<\/b><\/p>\n<ol>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Yes, this is a simplified explanation, there are entire textbooks written about this stuff.<\/span><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/red-light-applications-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/red-light-applications-in-photochemistry\/<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Don&rsquo;t worry, there&rsquo;s still room for you to synthesize 50 nearly identical derivatives of your favorite chromophore.<\/span><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/electron-donor-acceptor-eda-complexes-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/electron-donor-acceptor-eda-complexes-in-photochemistry\/<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Tucker, J. and Stephenson, C. R. J. \u00ab\u00a0Shining Light on Photoredox Catalysis: Theory and Synthetic Applications\u00a0\u00bb, <\/span><i><span style=\"font-weight: 400;\">Journal of Organic Chemistry<\/span><\/i><span style=\"font-weight: 400;\">, 2012, 77, 1617-1622.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. Photoredox Catalysis in Organic Chemistry. <\/span><i><span style=\"font-weight: 400;\">J. Org. Chem.<\/span><\/i><span style=\"font-weight: 400;\"> 2016, 81, 6898\u00e2\u02c6\u20196926. <\/span><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/acs.joc.6b01449\"><span style=\"font-weight: 400;\">https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/acs.joc.6b01449<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Romero, N., Nicewicz, \u00ab\u00a0Organic Photoredox Catalysis\u00a0\u00bb, <\/span><i><span style=\"font-weight: 400;\">Chemical Reviews, <\/span><\/i><span style=\"font-weight: 400;\">2016 (116), 10075-10166.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Marzo, L.; Pagire, S. K.; Reiser, O.; Ko\u00cc\u02c6nig, B. Visible light Photocatalysis: Does It Make a Difference in Organic Synthesis? <\/span><i><span style=\"font-weight: 400;\">Angew. Chem., Int. Ed<\/span><\/i><span style=\"font-weight: 400;\">. 2018, 57, 10034\u00e2\u02c6\u201910072.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Harper, K. Moschetta, E., Bordawekar, S., Wittenberger, S. \u00ab\u00a0A Laser Driven Flow Chemistry Platform for Scaling Photochemical Reactions with Visible light., <\/span><i><span style=\"font-weight: 400;\">ACS Central Science<\/span><\/i><span style=\"font-weight: 400;\">, 2019 (5), 109-115.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Justin P. Cole, Dian-Feng Chen, Max Kudisch, Ryan M. Pearson, Chern-Hooi Lim, and Garret M. Miyake, \u00ab\u00a0Organocatalyzed Birch Reduction Driven by Visible light, <\/span><i><span style=\"font-weight: 400;\">J. Am. Chem. Soc<\/span><\/i><span style=\"font-weight: 400;\">, 2020, 142, 13573-13581. <\/span><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jacs.0c05899\"><span style=\"font-weight: 400;\">https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jacs.0c05899<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Zuo, Z., Ahneman, D., Chu, L., Terrett, J., Doyle, A., Macmillan, D. \u00ab\u00a0Merging photoredox with nickel catalysis: Coupling of \u03b1-carboxyl sp<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">-carbons with aryl halides\u00a0\u00bb <\/span><i><span style=\"font-weight: 400;\">Science<\/span><\/i><span style=\"font-weight: 400;\">, 2014 (345), 437-440.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Bonfield, H.E., Knauber, T., L\u00c3\u00a9vesque, F. et al. Photons as a 21st century reagent. Nat Commun 11, 804 (2020) <\/span><a href=\"https:\/\/doi.org\/10.1038\/s41467-019-13988-4\"><span style=\"font-weight: 400;\">https:\/\/doi.org\/10.1038\/s41467-019-13988-4<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/evaluating-light-sources-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/evaluating-light-sources-in-photochemistry\/<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/determine-photon-flux-using-actinometry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/determine-photon-flux-using-actinometry\/<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Hatchard C.G.; Parker C.A. \u00ab\u00a0A new sensitive chemical actinometer. 2. Potassium ferrioxalate as a standard chemical actinometer.\u00a0\u00bb <\/span><i><span style=\"font-weight: 400;\">Proc. R. Soc. London, Ser. A<\/span><\/i><span style=\"font-weight: 400;\">. 1956, 235, 518-536.<\/span><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/standard-ferrioxalate-actinometer-protocol\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/standard-ferrioxalate-actinometer-protocol\/<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/fr\/photoreacteurs-accessoires-led-et-plus-encore\/#photoreactors\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/photoreactors-leds-accessories\/#photoreactors<\/span><\/a><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Terret, J. Cuthbertson, J. Shurtleff, V. MacMillan, D. \u00ab\u00a0Switching on elusive organometallic mechanisms with photoredox catalysis\u00a0\u00bb. <\/span><i><span style=\"font-weight: 400;\">Nature<\/span><\/i><span style=\"font-weight: 400;\">, 2015, 524, 330-334.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Primer, D., Karakaya, I. Tellis, J. Molander, G. \u00ab\u00a0Single-Electron Transmetallation: An Enabling Technology for Secondary Alkylboron Cross-Coupling\u00a0\u00bb. <\/span><i><span style=\"font-weight: 400;\">J. Am.Chem. Soc. <\/span><\/i><span style=\"font-weight: 400;\">2015, 137, 2195.<\/span><\/li>\n<li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Lim, C.H., Kudisch, M., Liu, B., Miyake, G. \u00ab\u00a0C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes\u00a0\u00bb <\/span><i><span style=\"font-weight: 400;\">J. Am. Chem. Soc.<\/span><\/i><span style=\"font-weight: 400;\"> 2018, 140, 24, 7667-7673.<\/span><\/li>\n<\/ol>\n<p>[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"<p>A quick guide to get you started with initial photochemistry reactions.<\/p>\n","protected":false},"author":1,"featured_media":23913,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"<h2>Setting Up Your Initial Photochemistry Reactions<\/h2><p><span style=\"font-weight: 400;\"><em>This is the third and final part of a three part series designed to help you get started by understanding light sources in photochemistry.\u00a0 Missed the start of the series where we cover the basics and core principles?\u00a0 No worries, <a href=\"\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\">you can read it here<\/a>...<\/em><\/span><\/p><p><span style=\"font-weight: 400;\">Visible light photoredox catalysis uses the excited states of metal complexes and organic dyes to perform energy transfer and single-electron transfer (SET) processes for an ever-increasing number of useful synthetic transformations.\u00a0 As should be apparent from reading <strong>Part 1<\/strong> (<a href=\"\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/\">\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\/<\/a>) and <strong>Part 2<\/strong> (<a href=\"\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\/\">\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\/<\/a>), we think photochemistry is pretty cool.\u00a0 But is it useful?\u00a0 The possibilities of where to start first can seem daunting.\u00a0 A standard reaction setup is imperative for reproducible chemistry from lab to lab enabling a low barrier to entry for the field.\u00a0 As you just read, step one to standardizing reactions is a better understanding of the light source.\u00a0 The second step is the reactor.\u00a0 Let's do a quick review before we start providing details on your <\/span>initial photochemistry reactions.<\/p><p><span style=\"font-weight: 400;\">First, it is a simple concept at first but needs to be stated.\u00a0 <strong>The only light that is useful to running your reaction is the light that actually makes its way into the flask<\/strong>.\u00a0 The bright blue light shining on the back of your hood isn\u2019t doing anything.\u00a0 For this reason, we have developed a series of photoreactors to maximize light intensity, control temperature and standardize reaction conditions that are currently in use in both industrial and academic settings (Ref 20).\u00a0 For use with a standardized setup, (the <a href=\"\/photoreactors-leds-accessories-old\/photoredox-box\/\">EvoluChem Photoredox Box<\/a>), we have selected and adapted four reactions from the literature as a convenient starting point for those new to photochemistry.\u00a0 Each reaction has been tested and validated in our equipment.\u00a0 Each is available as a part of bundle including photoreactor, sample holders, LED\u2019s and premixed reactions to run test reaction, as well as three substrate combinations of your choice (see <a href=\"\/photoreactors-leds-accessories\/photochemistry-starter-bundle\/\">https:\/\/hepatochem.com\/photoreactors-leds-accessories\/photochemistry-starter-bundle\/<\/a>).<\/span><\/p><h2>Experimental Details<\/h2><p><span style=\"font-weight: 400;\">Each reaction is performed in the Evoluchem PhotoRedOx box, equipped with either an 18W 450 nm or 365 nm <a href=\"\/photoreactors-leds-accessories\/led-evoluchem\/\">Evoluchem LED<\/a>.\u00a0 Reactions are performed in 4 mL vials equipped with a Teflon septa cap containing pre-weighed photocatalyst, co-catalyst base and reagents.\u00a0 Substrate solutions are added via syringe and the reaction is sparged with a N2 line via needle for 5 minutes prior to turning on the LED\u2019s.\u00a0 The reactor is equipped with a fan that holds the reaction temperature stable at ~30 \u00b0C.\u00a0 Reactions are run for 18-24 hr.\u00a0 Product analysis is performed by LC-MS.<\/span><\/p><h2>Initial Photochemistry Reactions:\u00a0C-C cross-coupling with amino acid decarboxylation<\/h2><p><em><span style=\"font-weight: 400;\">Adapted from Ref 14<br \/><\/span><\/em><span style=\"font-weight: 400;\">The first reaction that we want to highlight is an Iridium\/nickel catalyzed carbon-carbon bond formation as described by MacMillan and coworkers (Ref 14).\u00a0 This approach uses a commercially available iridium catalyst (Ir[dF(CF<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">)ppy]<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">(dtbbpy)PF<\/span><span style=\"font-weight: 400;\"><sub>6<\/sub> <\/span><span style=\"font-weight: 400;\">(structure in <strong>Figure 2<\/strong>) with a CFL bulb.\u00a0 The photoredox cycle activates a nickel catalyzed organometallic cycle for the coupling of \u03b1-carboxyl sp<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">-carbons with aryl halides.\u00a0 The nickel catalyst is formed <\/span><i><span style=\"font-weight: 400;\">in situ <\/span><\/i><span style=\"font-weight: 400;\">between NiCl<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub> <\/span><span style=\"font-weight: 400;\">with dtbbpy as a ligand.\u00a0 The reaction requires a base (Cs<\/span><span style=\"font-weight: 400;\">2<\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen. \u00a0 The reaction demonstrated coupling for a wide range of carboxylic acids with aryl bromides, iodides and select chlorides.\u00a0 The test reaction we have selected is the coupling of N-Boc-Valine and 4-bromoacetophenone which we have adapted from the reported procedure to use 450 nm LED instead of the CFL (<strong>Figure 8<\/strong>).\u00a0\u00a0<\/span><\/p>[caption id=\"attachment_8563\" align=\"aligncenter\" width=\"690\"]<img class=\"wp-image-8563 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure8.png\" alt=\"initial photochemistry reactions: Carbon-carbon formation between sp3 carbons and aryl halides\" width=\"690\" height=\"186\" \/> <strong>Figure 8:<\/strong> Carbon-carbon formation between sp3 carbons and aryl halides (adapted from Ref 14)[\/caption]<h2>Initial Photochemistry Reactions:\u00a0C-O bond formation<\/h2><p><span style=\"font-weight: 400;\">The second reaction that we have selected is also by MacMillan and coworkers using Ir\/Ni catalysis, however this time for C-O bond formation<\/span> <span style=\"font-weight: 400;\">(Ref 21).\u00a0 This reaction also uses (Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(dtbbpy)PF<sub>6<\/sub><\/span><span style=\"font-weight: 400;\">, NiCl<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub> <\/span><span style=\"font-weight: 400;\">and dtbbpy as a ligand.\u00a0 This reaction requires quinuclidine as an electron donor\/acceptor and an additional base.\u00a0 The reaction uses primary and secondary alcohol for C-O bond formation with aryl bromides.\u00a0 The reaction requires a base (K<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen. \u00a0 Nickel itself is unable to perform C-O couplings without the use of high temperatures due to the stability of nickel-alkoxide complexes.\u00a0 The photoredox cycle using a 450 nm LED and the iridium catalyst can activate this cycle at room temperature for a wide variety of alcohols and aryl bromides.\u00a0 The test reaction that we have selected is the coupling of cyclohexanol and 4-bromoacetophenone with 450 nm (<strong>Figure 9<\/strong>).<\/span><\/p>[caption id=\"attachment_8564\" align=\"aligncenter\" width=\"717\"]<img class=\"wp-image-8564 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure9.png\" alt=\"initial photochemistry reactions: C-O bond formation\" width=\"717\" height=\"225\" \/> <strong>Figure 9:<\/strong> C-O bond formation (Adapted from Ref 21)[\/caption]<h2>\u00a0<\/h2><h2>Initial Photochemistry Reactions:\u00a0C-C Cross coupling with BF<sub>3<\/sub>K reagents<\/h2><p><span style=\"font-weight: 400;\">The third reaction that we want to highlight is also a C-C bond formation, however this time using an alkyl BF<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">K reagent as the coupling partner.\u00a0 Molander and coworkers have performed a substantial amount of work using BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> reagents for photoredox catalyzed transformations.\u00a0 The reaction we are focusing on is the Iridium\/nickel catalyzed cross coupling of aryl bromides with secondary alkyl BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\">\u00a0reagents (<strong>Ref 22<\/strong>).\u00a0 BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> reagents are easy to handle, bench stable solid reagents useful for many cross-coupling reactions.\u00a0 This reaction works extremely well for a wide range of alkyl-BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\">\u00a0with aryl bromides and can very quickly be used to generate a large series of analogues. The reaction requires a base (Cs<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span><span style=\"font-weight: 400;\">CO<\/span><span style=\"font-weight: 400;\"><sub>3<\/sub><\/span><span style=\"font-weight: 400;\">) and sparging with nitrogen to remove oxygen.\u00a0 \u00a0 The test reaction we have selected uses cyclohexyl-BF<sub>3<\/sub>K<\/span><span style=\"font-weight: 400;\"> and 4-bromoacetophenone (Figure 10).\u00a0 We have modified the reaction condition to use Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(dtbbpy)PF<sub>6<\/sub><\/span> <span style=\"font-weight: 400;\">instead of Ir[dF(CF<sub>3<\/sub>)ppy]<sub>2<\/sub>(bpy)PF<sub>6<\/sub><\/span><span style=\"font-weight: 400;\">\u00a0<\/span><span style=\"font-weight: 400;\">(slightly different ligand), lowered the catalyst loading and use 450 nm LEDs instead of CFL.<\/span><\/p>[caption id=\"attachment_8565\" align=\"aligncenter\" width=\"749\"]<img class=\"wp-image-8565 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure10.png\" alt=\"initial photochemistry reactions: C-C cross-coupling with BF3K reagents \" width=\"749\" height=\"224\" \/> <strong>Figure 10:<\/strong>\u00a0 C-C cross-coupling with BF3K reagents (adapted from Ref 22)[\/caption]<h2>Initial Photochemistry Reactions:\u00a0C\u2212N Cross-Coupling via Photoexcitation of Nickel\u2212Amine Complexes<\/h2><p><span style=\"font-weight: 400;\">The final reaction we have selected is a carbon-nitrogen cross coupling reaction as described by Miyake and coworkers (<strong>Ref 23<\/strong>).\u00a0 This is the first reaction that we have selected that does not include an iridium catalyst or 450 nm LED.\u00a0 Here, the inexpensive NiBr<\/span><span style=\"font-weight: 400;\"><sub>2<\/sub><\/span> <span style=\"font-weight: 400;\">salt forms a photoactive complex with primary and secondary amines that can be excited by 365 nm LED\u2019s to give C-N bond formation products using aryl bromides.\u00a0 When excess amine is used, the addition of quinuclidine is not required. The reaction should be sparged with nitrogen to remove oxygen.\u00a0 \u00a0 Of note, this reaction is run at higher concentration than the previously selected reactions and the Ni-amine complex could be described as the photocatalyst for the reaction.\u00a0 We have selected the coupling of morpholine with 4-bromoacetophenone without quinuclidine.\u00a0\u00a0<\/span><\/p>[caption id=\"attachment_8566\" align=\"aligncenter\" width=\"742\"]<img class=\"wp-image-8566 size-full\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/10\/figure11.png\" alt=\"initial photochemistry reactions: C-N Cross-coupling reaction\" width=\"742\" height=\"208\" \/> <strong>Figure 11:\u00a0<\/strong> C-N Cross-coupling reaction (Ref 23)[\/caption]<p>\u00a0<\/p><p>We hope you have enjoyed this series on Photochemistry 101 and invite you to email us (<a href=\"mailto:info@hepatochem.com\">info@hepatochem.com<\/a>) or follow us on Twitter (<a href=\"https:\/\/twitter.com\/EvoluChem\">@EvoluChem<\/a>) to suggest more content and subject areas you would like us to cover.\u00a0 If you have any questions about the experiments above, or just find yourself stuck and looking for a good listener... drop us a line!\u00a0 Check out our starter bundle and give photoredox catalysis a try!<\/p><p><em><span style=\"font-weight: 400;\">You just read the third and final part of a three part series designed to help you get started in photochemistry.\u00a0 Below are links to all three parts of the series.\u00a0 Any questions?\u00a0 Send them to <a href=\"mailto:info@hepatochem.com\">info@hepatochem.com<\/a>, we'd love to hear from you!<br \/>Here's the entire series:<\/span><\/em><\/p><p><a href=\"\/photochemistry-101-everything-you-need-to-know-to-get-started-part-i\"><strong>Photochemistry 101, Part I: Everything You Need To Know To Get Started<\/strong><\/a><\/p><p><a href=\"\/photochemistry-101-part-ii-understanding-and-measuring-light-sources\"><strong>Photochemistry 101, Part II: Understanding and Measuring Light Sources<\/strong><\/a><\/p><p><a href=\"\/photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions\/\"><strong><span style=\"font-weight: 400;\"><strong>Photochemistry 101, Part III: Setting Up Your Initial Photochemistry Reactions<\/strong><\/span><\/strong><\/a><\/p><p>\u00a0<\/p><p><b>References<\/b><\/p><ol><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Yes, this is a simplified explanation, there are entire textbooks written about this stuff.\u00a0<\/span><\/li><li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/red-light-applications-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/red-light-applications-in-photochemistry\/<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Don\u2019t worry, there\u2019s still room for you to synthesize 50 nearly identical derivatives of your favorite chromophore.<\/span><\/li><li style=\"font-weight: 400;\"><a href=\"https:\/\/hepatochem.com\/electron-donor-acceptor-eda-complexes-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/electron-donor-acceptor-eda-complexes-in-photochemistry\/<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Tucker, J. and Stephenson, C. R. J.\u00a0 \u201cShining Light on Photoredox Catalysis:\u00a0 Theory and Synthetic Applications\u201d, <\/span><i><span style=\"font-weight: 400;\">Journal of Organic Chemistry<\/span><\/i><span style=\"font-weight: 400;\">, 2012, 77, 1617-1622.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886.\u00a0<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.\u00a0<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. Photoredox Catalysis in Organic Chemistry. <\/span><i><span style=\"font-weight: 400;\">J. Org. Chem.<\/span><\/i><span style=\"font-weight: 400;\"> 2016, 81, 6898\u22126926. <\/span><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/acs.joc.6b01449\"><span style=\"font-weight: 400;\">https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/acs.joc.6b01449<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Romero, N., Nicewicz, \u201cOrganic Photoredox Catalysis\u201d, <\/span><i><span style=\"font-weight: 400;\">Chemical Reviews, <\/span><\/i><span style=\"font-weight: 400;\">2016 (116), 10075-10166.\u00a0<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Marzo, L.; Pagire, S. K.; Reiser, O.; Ko\u0308nig, B. Visible light Photocatalysis: Does It Make a Difference in Organic Synthesis? <\/span><i><span style=\"font-weight: 400;\">Angew. Chem., Int. Ed<\/span><\/i><span style=\"font-weight: 400;\">. 2018, 57, 10034\u221210072.\u00a0\u00a0<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0\u00a0Harper, K.\u00a0 Moschetta, E., Bordawekar, S., Wittenberger, S.\u00a0 \u201cA Laser Driven Flow Chemistry Platform for Scaling Photochemical Reactions with Visible light., <\/span><i><span style=\"font-weight: 400;\">ACS Central Science<\/span><\/i><span style=\"font-weight: 400;\">, 2019 (5), 109-115.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Justin P. Cole, Dian-Feng Chen, Max Kudisch, Ryan M. Pearson, Chern-Hooi Lim, and Garret M. Miyake, \u201cOrganocatalyzed Birch Reduction Driven by Visible light, <\/span><i><span style=\"font-weight: 400;\">J. Am. Chem. Soc<\/span><\/i><span style=\"font-weight: 400;\">, 2020, 142, 13573-13581.\u00a0 <\/span><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jacs.0c05899\"><span style=\"font-weight: 400;\">https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jacs.0c05899<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0<\/span><span style=\"font-weight: 400;\">Zuo, Z., Ahneman, D., Chu, L., Terrett, J., Doyle, A., Macmillan, D.\u00a0 \u201cMerging photoredox with nickel catalysis:\u00a0 Coupling of \u03b1-carboxyl sp<\/span><span style=\"font-weight: 400;\">3<\/span><span style=\"font-weight: 400;\">-carbons with aryl halides\u201d <\/span><i><span style=\"font-weight: 400;\">Science<\/span><\/i><span style=\"font-weight: 400;\">, 2014 (345), 437-440.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Bonfield, H.E., Knauber, T., L\u00e9vesque, F. et al. Photons as a 21st century reagent. Nat Commun 11, 804 (2020) <\/span><a href=\"https:\/\/doi.org\/10.1038\/s41467-019-13988-4\"><span style=\"font-weight: 400;\">https:\/\/doi.org\/10.1038\/s41467-019-13988-4<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0<\/span><a href=\"https:\/\/hepatochem.com\/evaluating-light-sources-in-photochemistry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/evaluating-light-sources-in-photochemistry\/<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0<\/span><a href=\"https:\/\/hepatochem.com\/determine-photon-flux-using-actinometry\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/determine-photon-flux-using-actinometry\/<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0\u00a0Hatchard C.G.; Parker C.A. \u201cA new sensitive chemical actinometer. 2. Potassium ferrioxalate as a standard chemical actinometer.\u201d <\/span><i><span style=\"font-weight: 400;\">Proc. R. Soc. London, Ser. A<\/span><\/i><span style=\"font-weight: 400;\">. 1956, 235, 518-536.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0<\/span><a href=\"https:\/\/hepatochem.com\/standard-ferrioxalate-actinometer-protocol\/\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/standard-ferrioxalate-actinometer-protocol\/<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0<\/span><a href=\"https:\/\/hepatochem.com\/photoreactors-leds-accessories\/#photoreactors\"><span style=\"font-weight: 400;\">https:\/\/hepatochem.com\/photoreactors-leds-accessories\/#photoreactors<\/span><\/a><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Terret, J. Cuthbertson, J.\u00a0 Shurtleff, V. MacMillan, D. \u201cSwitching on elusive organometallic mechanisms with photoredox catalysis\u201d.\u00a0 <\/span><i><span style=\"font-weight: 400;\">Nature<\/span><\/i><span style=\"font-weight: 400;\">, 2015, 524, 330-334.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Primer, D., Karakaya, I.\u00a0 Tellis, J.\u00a0 Molander, G.\u00a0 \u201cSingle-Electron Transmetallation:\u00a0 An Enabling Technology for Secondary Alkylboron Cross-Coupling\u201d.\u00a0 <\/span><i><span style=\"font-weight: 400;\">J. Am.Chem. Soc. <\/span><\/i><span style=\"font-weight: 400;\">\u00a02015, 137, 2195.<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">\u00a0Lim, C.H., Kudisch, M., Liu, B., Miyake, G. \u201cC-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes\u201d <\/span><i><span style=\"font-weight: 400;\">J. Am. Chem. Soc.<\/span><\/i><span style=\"font-weight: 400;\"> 2018, 140, 24, 7667-7673.<\/span><\/li><\/ol>","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[486,483,489,487],"tags":[501,491],"class_list":["post-24938","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-educational","category-feature-2","category-featured-articles","category-photoredox","tag-initial-reactions","tag-photochemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Photochemistry 101, Part III: Setting Up Your Initial Photochemistry Reactions<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/hepatochem.com\/fr\/photochemistry-101-part-iii-setting-up-your-initial-photochemistry-reactions\/\" \/>\n<meta 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