{"id":24849,"date":"2023-03-15T18:16:40","date_gmt":"2023-03-15T22:16:40","guid":{"rendered":"https:\/\/hepatochem.com\/photochemistry-surprises\/"},"modified":"2023-03-15T18:16:40","modified_gmt":"2023-03-15T22:16:40","slug":"photochemistry-surprises","status":"publish","type":"post","link":"https:\/\/hepatochem.com\/fr\/photochemistry-surprises\/","title":{"rendered":"Photochemistry Surprises!!!"},"content":{"rendered":"

[et_pb_section fb_built=\u00a0\u00bb1″ admin_label=\u00a0\u00bbsection\u00a0\u00bb _builder_version=\u00a0\u00bb4.16″ global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][et_pb_row admin_label=\u00a0\u00bbrow\u00a0\u00bb _builder_version=\u00a0\u00bb4.20.0″ background_size=\u00a0\u00bbinitial\u00a0\u00bb background_position=\u00a0\u00bbtop_left\u00a0\u00bb background_repeat=\u00a0\u00bbrepeat\u00a0\u00bb width=\u00a0\u00bb100%\u00a0\u00bb custom_padding=\u00a0\u00bb|10px||10px|false|true\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][et_pb_column type=\u00a0\u00bb4_4″ _builder_version=\u00a0\u00bb4.16″ 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_image src=\u00a0\u00bbhttps:\/\/hepatochem.com\/wp-content\/uploads\/2023\/03\/Blue-Wait-What-square.jpg\u00a0\u00bb alt=\u00a0\u00bbUnexpected azepinone formation\u00a0\u00bb title_text=\u00a0\u00bbBlue Wait What square\u00a0\u00bb _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb width=\u00a0\u00bb60%\u00a0\u00bb module_alignment=\u00a0\u00bbcenter\u00a0\u00bb custom_padding=\u00a0\u00bb32px||32px||true|false\u00a0\u00bb hover_enabled=\u00a0\u00bb0″ global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb sticky_enabled=\u00a0\u00bb0″][\/et_pb_image][et_pb_text admin_label=\u00a0\u00bbText\u00a0\u00bb _builder_version=\u00a0\u00bb4.20.0″ header_5_line_height=\u00a0\u00bb1.8em\u00a0\u00bb background_size=\u00a0\u00bbinitial\u00a0\u00bb background_position=\u00a0\u00bbtop_left\u00a0\u00bb background_repeat=\u00a0\u00bbrepeat\u00a0\u00bb hover_enabled=\u00a0\u00bb0″ global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb sticky_enabled=\u00a0\u00bb0″]<\/p>\n

For this month’s newsletter we thought we would look at an unexpected surprise in photochemistry. A project with one of those moments where \u00ab\u00a0hey that’s weird, and very wrong\u00a0\u00bb turns into something bigger and better. It takes a bold decision, a little stubbornness and some ingenuity, to turn a potential dead end into a new opportunity.<\/strong><\/h5>\n

<\/strong><\/p>\n

This brings us to a recent paper by the A. Stephen K. Hashmi and coworkers in Nature Communications<\/em> titled \u00ab\u00a0An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction<\/a>\u00a0\u00bb (Open Access) (Ref 1). \u00ab\u00a0Unexpected synthesis\u00a0\u00bb is not a topic that shows up all that often in the literature. Synthesis is planned, meticulously so. Unexpected synthesis is usually the black tar on the bottom of your flask that you try to scrape out with a spatula before throwing the whole works in the trash. And when \u00ab\u00a0unexpected\u00a0\u00bb happens to give you something useful, by the time you get around to writing up the paper usually there is a well-reasoned explanation for why you planned it in the first place. So, it’s refreshing to see all of that stated up front.<\/p>\n

The authors were attempting to look at the reactivity of 2-aryloxyaryl nitrenes. This was based on their previous work using sulfilimines as nitrene precursors via both photocatalysis and Rh catalysis to generate carbazoles (Figure 1A). For this work, the expectation was that they would form the 10H<\/em>-phenoxazine derivatives upon irradiation of the sulfilimine via a nitrene intermediate. Instead, they formed an azepinone, which in case you aren’t up on your heterocycle nomenclature is the oxidized form of an azepine which is in turn a 7-membered unsaturated heterocycle containing 1 nitrogen (Figure 1B). Side note: 7 membered rings will always look goofy to us. If you can draw one freehand with a regular shape you are better than us. It always just looks like an accidental mishappened cyclohexane or 1 carbon short of an octane. It just never looks right. Maybe that’s just us.<\/p>\n

Figure 1:<\/strong> Unexpected azepinone formation (Figure adapted from Ref 1)<\/p>\n

A. Previous Work<\/strong><\/p>\n

[\/et_pb_text][et_pb_image src=\u00a0\u00bbhttps:\/\/hepatochem.com\/wp-content\/uploads\/2023\/03\/Photochemical-surprise-Figure-1-e1678917270219.jpg\u00a0\u00bb title_text=\u00a0\u00bbPhotochemical surprise – Figure 1″ _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][\/et_pb_image][et_pb_text _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb]<\/p>\n

B. This Work<\/strong><\/p>\n

[\/et_pb_text][et_pb_image src=\u00a0\u00bbhttps:\/\/hepatochem.com\/wp-content\/uploads\/2023\/03\/Photochemical-surprise-Figure-1-1-e1678917360610.jpg\u00a0\u00bb title_text=\u00a0\u00bbPhotochemical surprise – Figure 1″ _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][\/et_pb_image][et_pb_text _builder_version=\u00a0\u00bb4.20.4″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb]<\/p>\n

Azepinones are found in many natural products and pharmaceuticals as privileged structures. Methods to make these compounds usually require a strong base, high power UV light or metal catalysis. A metal free visible light catalysis method for making a series azepinones inexpensively? Yeah, that could work.<\/p>\n

But first, how did they get here? And can they do it again?<\/p>\n

Optimization of the method found a few key features. First, blue light (40% conversion) performed better than UVA (17%). Switching to solvents other than THF was detrimental. Using the azide in place of the sulfilimine and adding 10 equiv. of H2O pushed the yield to 65%. And finally, 0.5 equiv. p-toluenesulfonic acid was best at 83% for this model system. Other protic acids and Lewis acids showed no improvement. And ultimately, no reaction was observed in the dark.<\/span><\/p>\n

Figure 2:<\/strong> Model reaction for generation of a series of azepinone derivatives<\/p>\n

[\/et_pb_text][et_pb_image src=\u00a0\u00bbhttps:\/\/hepatochem.com\/wp-content\/uploads\/2023\/03\/Photochemical-surprise-Figure-2.jpg\u00a0\u00bb title_text=\u00a0\u00bbPhotochemical surprise – Figure 2″ _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][\/et_pb_image][et_pb_text _builder_version=\u00a0\u00bb4.20.4″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb hover_enabled=\u00a0\u00bb0″ global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb sticky_enabled=\u00a0\u00bb0″]<\/p>\n

With reaction in hand, the authors then looked at an extensive substrate scope with several of the resulting azepinone structures further derivatized to more complex structures. The aryl azide (R1) supported chloro, trifluormethyl, methyl and methoxy groups and the arene (R2) supported alkyl and arene and thiophenyl substituents. The phenol can be easily protected and\/or converted with additional coupling reactions for more complex products. Ultimately, this method looks to be an inexpensive method for generating a library of azepinone derivatives.<\/p>\n

For the mechanism? Reactions with Da\u201a\u201aO gave 50% deuterium incorporation into the CHa\u201a\u201a on the azepinone and 95% in the phenol. 18<\/sup>O-labeling experiments with Ha\u201a\u201a18<\/sup>O gave 90% 18<\/sup>O incorporation into the carbonyl. Ultimately, DFT and the labeling experiments support a mechanism proposing the following cascade reaction, photochemical generation of a 2-aryloxyaryl nitrene, [2+1] annulation, ring expansion, and addition of water.<\/p>\n

Figure 3:<\/strong> Selected steps in the proposed cascade reaction<\/p>\n

[\/et_pb_text][et_pb_image src=\u00a0\u00bbhttps:\/\/hepatochem.com\/wp-content\/uploads\/2023\/03\/Photochemical-surprise-Figure-3-scaled.jpg\u00a0\u00bb title_text=\u00a0\u00bbPhotochemical surprise – Figure 3″ _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][\/et_pb_image][et_pb_text _builder_version=\u00a0\u00bb4.20.0″ _module_preset=\u00a0\u00bbdefault\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb]<\/p>\n

In the end, this unexpected result that wasn’t discarded or ignored ended up resulting in an inexpensive versatile reaction suitable for a generating libraries of an important. Great work!<\/p>\n

<\/strong><\/p>\n

References:<\/strong><\/p>\n

Song, L.; Tian, X.; Farshadfar, K.; Shiri, F.; Rominger, F.; Ariafard, A.; Hashmi, A. S. K. An Unexpected Synthesis of Azepinone Derivatives through a Metal-Free Photochemical Cascade Reaction. Nat. Commun. 2023, 14 (1), 831. https:\/\/doi.org\/10.1038\/s41467-023-36190-z<\/a>.<\/p>\n

[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"

Featuring a project where \u201chey that\u2019s weird & very wrong\u201d turns into something fantastic: Bold decisions, stubbornness & ingenuity result in a new opportunity.<\/p>\n","protected":false},"author":1,"featured_media":24851,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"

\r\n
\r\n
\"photochemistry<\/a><\/h5>\r\n
For this month\u2019s newsletter we thought we would look at an unexpected surprise in photochemistry. A project with one of those moments where \u201chey that\u2019s weird, and very wrong\u201d turns into something bigger and better. It takes a bold decision, a little stubbornness and some ingenuity, to turn a potential dead end into a new opportunity.<\/strong><\/h5>\r\nThis brings us to a recent paper by the A. Stephen K. Hashmi and coworkers in Nature Communications<\/em> titled \u201cAn unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction<\/a>\u201d (Open Access) (Ref 1). \u201cUnexpected synthesis\u201d is not a topic that shows up all that often in the literature. Synthesis is planned, meticulously so. Unexpected synthesis is usually the black tar on the bottom of your flask that you try to scrape out with a spatula before throwing the whole works in the trash. And when \u201cunexpected\u201d happens to give you something useful, by the time you get around to writing up the paper usually there is a well-reasoned explanation for why you planned it in the first place. So, it\u2019s refreshing to see all of that stated up front.\r\n\r\nThe authors were attempting to look at the reactivity of 2-aryloxyaryl nitrenes. This was based on their previous work using sulfilimines as nitrene precursors via both photocatalysis and Rh catalysis to generate carbazoles (Figure 1A). For this work, the expectation was that they would form the 10H<\/em>-phenoxazine derivatives upon irradiation of the sulfilimine via a nitrene intermediate. Instead, they formed an azepinone, which in case you aren\u2019t up on your heterocycle nomenclature is the oxidized form of an azepine which is in turn a 7-membered unsaturated heterocycle containing 1 nitrogen (Figure 1B). Side note: 7 membered rings will always look goofy to us. If you can draw one freehand with a regular shape you are better than us. It always just looks like an accidental mishappened cyclohexane or 1 carbon short of an octane. It just never looks right. Maybe that\u2019s just us.\r\n\r\nFigure 1:<\/strong> Unexpected azepinone formation (Figure adapted from Ref 1)\r\n\r\nA. Previous Work<\/strong>\r\n\r\n\"\"<\/a>\r\n\r\n<\/div>\r\nB.\u00a0 This Work<\/strong>\r\n\r\n<\/div>\r\nAzepinones are found in many natural products and pharmaceuticals as privileged structures. Methods to make these compounds usually require a strong base, high power UV light or metal catalysis. A metal free visible light catalysis method for making a series azepinones inexpensively? Yeah, that could work.\r\n\r\n\"\"<\/a>\r\n\r\nBut first, how did they get here? And can they do it again?\r\n\r\nOptimization of the method found a few key features. First, blue light (40% conversion) performed better than UVA (17%). Switching to solvents other than THF was detrimental. Using the azide in place of the sulfilimine and adding 10 equiv. of H\u2082O pushed the yield to 65%. And finally, 0.5 equiv. p<\/em>-toluenesulfonic acid was best at 83% for this model system. Other protic acids and Lewis acids showed no improvement. And ultimately, no reaction was observed in the dark.\r\n\r\nFigure 2:<\/strong> Model reaction for generation of a series of azepinone derivatives\r\n\r\n\"\"<\/a>\r\n
\r\n
\r\n\r\nWith reaction in hand, the authors then looked at an extensive substrate scope with several of the resulting azepinone structures further derivatized to more complex structures. The aryl azide (R1) supported chloro, trifluormethyl, methyl and methoxy groups and the arene (R2) supported alkyl and arene and thiophenyl substituents. The phenol can be easily protected and\/or converted with additional coupling reactions for more complex products. Ultimately, this method looks to be an inexpensive method for generating a library of azepinone derivatives.\r\n\r\nFor the mechanism? Reactions with D\u2082O gave 50% deuterium incorporation into the CH\u2082 on the azepinone and 95% in the phenol. 18<\/sup>O-labeling experiments with H\u208218<\/sup>O gave 90% 18<\/sup>O incorporation into the carbonyl. Ultimately, DFT and the labeling experiments support a mechanism proposing the following cascade reaction, photochemical generation of a 2-aryloxyaryl nitrene, [2+1] annulation, ring expansion, and addition of water.\r\n\r\nFigure 3:<\/strong> Selected steps in the proposed cascade reaction\r\n\r\n\"\"<\/a>\r\n\r\n<\/div>\r\n
\r\n
\r\n\r\nIn the end, this unexpected result that wasn\u2019t discarded or ignored ended up resulting in an inexpensive versatile reaction suitable for a generating libraries of an important.\u00a0 Great work!\r\n\r\n\u00a0\r\n\r\nReferences:<\/strong>\r\n\r\nSong, L.; Tian, X.; Farshadfar, K.; Shiri, F.; Rominger, F.; Ariafard, A.; Hashmi, A. S. K. An Unexpected Synthesis of Azepinone Derivatives through a Metal-Free Photochemical Cascade Reaction. Nat. Commun. 2023, 14 (1), 831. https:\/\/doi.org\/10.1038\/s41467-023-36190-z<\/a>.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[483,478],"tags":[],"class_list":["post-24849","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-feature-2","category-scientific-literature"],"yoast_head":"\nPhotochemistry Surprises!!!<\/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-surprises\/\" \/>\n<meta name=\"twitter:label1\" content=\"\u00c9crit par\" \/>\n\t<meta name=\"twitter:data1\" content=\"admin\" \/>\n\t<meta name=\"twitter:label2\" content=\"Dur\u00e9e de lecture estim\u00e9e\" \/>\n\t<meta name=\"twitter:data2\" content=\"5 minutes\" \/>\n<script type=\"application\/ld+json\" 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