{"id":25628,"date":"2018-06-19T18:08:18","date_gmt":"2018-06-20T01:08:18","guid":{"rendered":"https:\/\/hepatochem.com\/electrophile-substrate-functionality-and-catalyst-effects-in-the-synthesis-of-%ce%b1%e2%80%90mono-and-di%e2%80%90substituted-benzylamines-via-visible%e2%80%90light-photoredox-catalysis-in-flow\/"},"modified":"2018-06-19T18:08:18","modified_gmt":"2018-06-20T01:08:18","slug":"electrophile-substrate-functionality-and-catalyst-effects-in-the-synthesis-of-%ce%b1%e2%80%90mono-and-di%e2%80%90substituted-benzylamines-via-visible%e2%80%90light-photoredox-catalysis-in-flow","status":"publish","type":"post","link":"https:\/\/hepatochem.com\/euro\/electrophile-substrate-functionality-and-catalyst-effects-in-the-synthesis-of-%ce%b1%e2%80%90mono-and-di%e2%80%90substituted-benzylamines-via-visible%e2%80%90light-photoredox-catalysis-in-flow\/","title":{"rendered":"Electrophile, Substrate Functionality, and Catalyst Effects in the Synthesis of \u03b1\u2010Mono and Di\u2010Substituted Benzylamines via Visible\u2010Light Photoredox Catalysis in Flow"},"content":{"rendered":"<p>[et_pb_section fb_built=&#8221;1&#8243; admin_label=&#8221;section&#8221; _builder_version=&#8221;4.16&#8243; global_colors_info=&#8221;{}&#8221;][et_pb_row admin_label=&#8221;row&#8221; _builder_version=&#8221;4.16&#8243; background_size=&#8221;initial&#8221; background_position=&#8221;top_left&#8221; background_repeat=&#8221;repeat&#8221; global_colors_info=&#8221;{}&#8221;][et_pb_column type=&#8221;4_4&#8243; _builder_version=&#8221;4.16&#8243; custom_padding=&#8221;|||&#8221; global_colors_info=&#8221;{}&#8221; custom_padding__hover=&#8221;|||&#8221;][et_pb_text admin_label=&#8221;Text&#8221; _builder_version=&#8221;4.20.4&#8243; background_size=&#8221;initial&#8221; background_position=&#8221;top_left&#8221; background_repeat=&#8221;repeat&#8221; hover_enabled=&#8221;0&#8243; global_colors_info=&#8221;{}&#8221; sticky_enabled=&#8221;0&#8243;]<\/p>\n<p><strong>Abstract<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignright size-medium wp-image-8355\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/09\/Screen-Shot-2020-09-01-at-9.15.03-PM-300x224.png\" alt=\"\" width=\"300\" height=\"224\" srcset=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/09\/Screen-Shot-2020-09-01-at-9.15.03-PM-300x224.png 300w, https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/09\/Screen-Shot-2020-09-01-at-9.15.03-PM.png 449w\" sizes=\"(max-width: 300px) 100vw, 300px\" \/>We report herein the facile and one&#8221;pot synthesis of \u03b1&#8221;mono&#8221; and di&#8221;substituted benzylamines from cheap and readily available \u03b1&#8221;amino acids, via photocatalytic decarboxylative arylation in flow. This enables to access intermediates and building blocks that are difficult to obtain via other synthetic routes, but are key for the manufacture of pharmaceuticals, agrochemicals, and fine chemicals. The optimal decarboxylative conditions were identified through a high&#8221;throughput evaluation of catalysts, organic or inorganic bases, ligands, and reaction parameters (i.&#8221;\u2030e., contact time, temperatures, and photoelectron power). The reaction turned out to be electronically controlled as the yields increased with increasing electron&#8221;density on the aryl moiety. The results were correlated with the redox properties of the photocatalysts, deriving catalyst structure&#8221;performance relationships which can facilitate the future identification of even better materials. In addition, compared to traditional batch chemistry, the use of a flow protocol led to quicker reactions (30&#8243;\u2026min instead of 12\u201372&#8243;\u2026h) and ensured more predictable reaction scale&#8221;ups.<\/p>\n<p><strong>Authors:<\/strong> <a id=\"a1_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Vil%C3%A9%2C+Gianvito\" data-id=\"a1\" data-db-target-for=\"a1\" aria-controls=\"a1\" aria-haspopup=\"true\">Dr. Gianvito Vil\u00e9, <\/a><a id=\"a2_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Richard-Bildstein%2C+Sylvia\" data-id=\"a2\" data-db-target-for=\"a2\" aria-controls=\"a2\" aria-haspopup=\"true\">Dr. Sylvia Richard&#8221;Bildstein<\/a>, <a id=\"a3_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Lhuillery%2C+Arnaud\" data-id=\"a3\" data-db-target-for=\"a3\" aria-controls=\"a3\" aria-haspopup=\"true\">Arnaud Lhuillery<\/a>,<a id=\"a4_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Rueedi%2C+Georg\" data-id=\"a4\" data-db-target-for=\"a4\" aria-controls=\"a4\" aria-haspopup=\"true\">Dr. Georg Rueedi<\/a><\/p>\n<p><strong>Link:<\/strong> <a href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/abs\/10.1002\/cctc.201800754\" target=\"_blank\" rel=\"noopener noreferrer\">https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/abs\/10.1002\/cctc.201800754<\/a><\/p>\n<p>[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Abstract We report herein the facile and one&#8221;pot synthesis of \u03b1&#8221;mono&#8221; and di&#8221;substituted benzylamines from cheap and readily available \u03b1&#8221;amino acids, via photocatalytic decarboxylative arylation in flow. This enables to access intermediates and building blocks that are difficult to obtain via other synthetic routes, but are key for the manufacture of pharmaceuticals, agrochemicals, and fine [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":25629,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"<!DOCTYPE html PUBLIC \"-\/\/W3C\/\/DTD HTML 4.0 Transitional\/\/EN\" \"http:\/\/www.w3.org\/TR\/REC-html40\/loose.dtd\">\r\n<html><body><strong>Abstract<\/strong>\r\n\r\n<img class=\"alignright size-medium wp-image-8355\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/09\/Screen-Shot-2020-09-01-at-9.15.03-PM-300x224.png\" alt=\"\" width=\"300\" height=\"224\">We report herein the facile and one\"pot synthesis of \u03b1\"mono\" and di\"substituted benzylamines from cheap and readily available \u03b1\"amino acids, via photocatalytic decarboxylative arylation in flow. This enables to access intermediates and building blocks that are difficult to obtain via other synthetic routes, but are key for the manufacture of pharmaceuticals, agrochemicals, and fine chemicals. The optimal decarboxylative conditions were identified through a high\"throughput evaluation of catalysts, organic or inorganic bases, ligands, and reaction parameters (i.\"\u2030e., contact time, temperatures, and photoelectron power). The reaction turned out to be electronically controlled as the yields increased with increasing electron\"density on the aryl moiety. The results were correlated with the redox properties of the photocatalysts, deriving catalyst structure\"performance relationships which can facilitate the future identification of even better materials. In addition, compared to traditional batch chemistry, the use of a flow protocol led to quicker reactions (30\"\u2026min instead of 12\u201372\"\u2026h) and ensured more predictable reaction scale\"ups.\r\n\r\n<strong>Authors:<\/strong> <a id=\"a1_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Vil%C3%A9%2C+Gianvito\" data-id=\"a1\" data-db-target-for=\"a1\" aria-controls=\"a1\" aria-haspopup=\"true\">Dr. Gianvito Vil\u00c3\u00a9, <\/a><a id=\"a2_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Richard-Bildstein%2C+Sylvia\" data-id=\"a2\" data-db-target-for=\"a2\" aria-controls=\"a2\" aria-haspopup=\"true\">Dr. Sylvia Richard\"Bildstein<\/a>, <a id=\"a3_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Lhuillery%2C+Arnaud\" data-id=\"a3\" data-db-target-for=\"a3\" aria-controls=\"a3\" aria-haspopup=\"true\">Arnaud Lhuillery<\/a>,<a id=\"a4_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Rueedi%2C+Georg\" data-id=\"a4\" data-db-target-for=\"a4\" aria-controls=\"a4\" aria-haspopup=\"true\">Dr. Georg Rueedi<\/a>\r\n\r\n<strong>Link:<\/strong> <a href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/abs\/10.1002\/cctc.201800754\" target=\"_blank\" rel=\"noopener noreferrer\">https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/abs\/10.1002\/cctc.201800754<\/a><\/body><\/html>\r\n","_et_gb_content_width":"","_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_post_was_ever_published":false},"categories":[680],"tags":[],"class_list":["post-25628","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-featured-articles"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.8 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Electrophile, Substrate Functionality, and Catalyst Effects in the Synthesis of \u03b1\u2010Mono and Di\u2010Substituted Benzylamines via Visible\u2010Light Photoredox Catalysis in Flow<\/title>\n<meta name=\"robots\" content=\"index, follow, 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