{"id":24969,"date":"2020-06-22T12:47:14","date_gmt":"2020-06-22T19:47:14","guid":{"rendered":"https:\/\/hepatochem.com\/photocatalytic-%ce%b1%e2%80%90tertiary-amine-synthesis-via-c%e2%88%92h-alkylation-of-unmasked-primary-amines\/"},"modified":"2020-06-22T12:47:14","modified_gmt":"2020-06-22T19:47:14","slug":"photocatalytic-%ce%b1%e2%80%90tertiary-amine-synthesis-via-c%e2%88%92h-alkylation-of-unmasked-primary-amines","status":"publish","type":"post","link":"https:\/\/hepatochem.com\/fr\/photocatalytic-%ce%b1%e2%80%90tertiary-amine-synthesis-via-c%e2%88%92h-alkylation-of-unmasked-primary-amines\/","title":{"rendered":"Photocatalytic \u03b1\u2010Tertiary Amine Synthesis via C\u2212H Alkylation of Unmasked Primary Amines"},"content":{"rendered":"<p>[et_pb_section fb_built=\u00a0\u00bb1&Prime; _builder_version=\u00a0\u00bb4.16&Prime; global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\u00a0\u00bb][et_pb_row _builder_version=\u00a0\u00bb4.16&Prime; background_size=\u00a0\u00bbinitial\u00a0\u00bb background_position=\u00a0\u00bbtop_left\u00a0\u00bb background_repeat=\u00a0\u00bbrepeat\u00a0\u00bb global_colors_info=\u00a0\u00bb{}\u00a0\u00bb theme_builder_area=\u00a0\u00bbpost_content\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\u00bb4.20.4&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 sticky_enabled=\u00a0\u00bb0&Prime;]<\/p>\n<p><strong>Abtract<br \/><\/strong><\/p>\n<div id=\"attachment_8223\" style=\"width: 310px\" class=\"wp-caption alignright\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-8223\" class=\"wp-image-8223 size-medium\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/07\/Screen-Shot-2020-07-22-at-3.54.52-PM-300x241.png\" alt=\"\" width=\"300\" height=\"241\" \/><p id=\"caption-attachment-8223\" class=\"wp-caption-text\">A)\u00a0\u00bb\u2026Prior art for catalytic \u03b1-C-H alkylation of primary amines; B)\u00a0\u00bb\u2026This work. EWG=electron\u00a0\u00bbwithdrawing group.<\/p><\/div>\n<p>A practical, catalytic entry to \u03b1,\u03b1,\u03b1\u00a0\u00bbtrisubstituted (\u03b1\u00a0\u00bbtertiary) primary amines by C-H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100&Prime;\u2030% atom\u00a0\u00bbeconomy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of \u03b1\u00a0\u00bbtertiary amines, or their corresponding \u03b3-lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging \u03b1\u00a0\u00bbtertiary primary amines.<\/p>\n<p><strong>Authors:<\/strong> <a id=\"a1_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Ryder%2C+Alison+S+H\" data-id=\"a1\" data-db-target-for=\"a1\" aria-controls=\"a1\" aria-haspopup=\"true\">Alison S. H. Ryder<\/a><a id=\"a2_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Cunningham%2C+William+B\" data-id=\"a2\" data-db-target-for=\"a2\" aria-controls=\"a2\" aria-haspopup=\"true\">Dr. William B. Cunningham<\/a><a id=\"a3_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Ballantyne%2C+George\" data-id=\"a3\" data-db-target-for=\"a3\" aria-controls=\"a3\" aria-haspopup=\"true\">George Ballantyne<\/a><a id=\"a4_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Mules%2C+Tom\" data-id=\"a4\" data-db-target-for=\"a4\" aria-controls=\"a4\" aria-haspopup=\"true\">Tom Mules<\/a><a id=\"a5_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Kinsella%2C+Anna+G\" data-id=\"a5\" data-db-target-for=\"a5\" aria-controls=\"a5\" aria-haspopup=\"true\">Anna G. Kinsella<\/a><a id=\"a6_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Turner-Dore%2C+Jacob\" data-id=\"a6\" data-db-target-for=\"a6\" aria-controls=\"a6\" aria-haspopup=\"true\">Jacob Turner\u00a0\u00bbDore<\/a><a id=\"a7_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Alder%2C+Catherine+M\" data-id=\"a7\" data-db-target-for=\"a7\" aria-controls=\"a7\" aria-haspopup=\"true\">Dr. Catherine M. Alder<\/a><a id=\"a8_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Edwards%2C+Lee+J\" data-id=\"a8\" data-db-target-for=\"a8\" aria-controls=\"a8\" aria-haspopup=\"true\">Lee J. Edwards<\/a><a id=\"a9_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=McKay%2C+Blandine+S+J\" data-id=\"a9\" data-db-target-for=\"a9\" aria-controls=\"a9\" aria-haspopup=\"true\">Dr. Blandine S. J. McKay<\/a><a id=\"a10_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Grayson%2C+Matthew+N\" data-id=\"a10\" data-db-target-for=\"a10\" aria-controls=\"a10\" aria-haspopup=\"true\">Dr. Matthew N. Grayson<\/a><a id=\"a11_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Cresswell%2C+Alexander+J\" data-id=\"a11\" data-db-target-for=\"a11\" aria-controls=\"a11\" aria-haspopup=\"true\">Dr. Alexander J. Cresswell<\/a><\/p>\n<p><strong>Link<\/strong><br \/><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/anie.202005294#.Xr2aciKIkvU.twitter\" target=\"_blank\" rel=\"noopener noreferrer\">https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/anie.202005294#.Xr2aciKIkvU.twitter<\/a><\/p>\n<p>&nbsp;<\/p>\n<p>[\/et_pb_text][\/et_pb_column][\/et_pb_row][\/et_pb_section]<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Abtract A practical, catalytic entry to \u03b1,\u03b1,\u03b1\u00a0\u00bbtrisubstituted (\u03b1\u00a0\u00bbtertiary) primary amines by C-H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100&Prime;\u2030% atom\u00a0\u00bbeconomy. Our strategy, which [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":24971,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"on","_et_pb_old_content":"<p><strong>Abtract<br \/><\/strong><\/p>[caption id=\"attachment_8223\" align=\"alignright\" width=\"300\"]<img class=\"wp-image-8223 size-medium\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/07\/Screen-Shot-2020-07-22-at-3.54.52-PM-300x241.png\" alt=\"\" width=\"300\" height=\"241\" \/> A)\u2005Prior art for catalytic \u03b1\u2010C\u2212H alkylation of primary amines; B)\u2005This work. EWG=electron\u2010withdrawing group.[\/caption]<p>A practical, catalytic entry to \u03b1,\u03b1,\u03b1\u2010trisubstituted (\u03b1\u2010tertiary) primary amines by C\u2212H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100\u2009% atom\u2010economy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of \u03b1\u2010tertiary amines, or their corresponding \u03b3\u2010lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging \u03b1\u2010tertiary primary amines.<\/p><p><strong>Authors:<\/strong> <a id=\"a1_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Ryder%2C+Alison+S+H\" data-id=\"a1\" data-db-target-for=\"a1\" aria-controls=\"a1\" aria-haspopup=\"true\">Alison S. H. Ryder<\/a>\u00a0<a id=\"a2_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Cunningham%2C+William+B\" data-id=\"a2\" data-db-target-for=\"a2\" aria-controls=\"a2\" aria-haspopup=\"true\">Dr. William B. Cunningham<\/a>\u00a0<a id=\"a3_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Ballantyne%2C+George\" data-id=\"a3\" data-db-target-for=\"a3\" aria-controls=\"a3\" aria-haspopup=\"true\">George Ballantyne<\/a>\u00a0<a id=\"a4_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Mules%2C+Tom\" data-id=\"a4\" data-db-target-for=\"a4\" aria-controls=\"a4\" aria-haspopup=\"true\">Tom Mules<\/a>\u00a0<a id=\"a5_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Kinsella%2C+Anna+G\" data-id=\"a5\" data-db-target-for=\"a5\" aria-controls=\"a5\" aria-haspopup=\"true\">Anna G. Kinsella<\/a>\u00a0<a id=\"a6_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Turner-Dore%2C+Jacob\" data-id=\"a6\" data-db-target-for=\"a6\" aria-controls=\"a6\" aria-haspopup=\"true\">Jacob Turner\u2010Dore<\/a>\u00a0<a id=\"a7_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Alder%2C+Catherine+M\" data-id=\"a7\" data-db-target-for=\"a7\" aria-controls=\"a7\" aria-haspopup=\"true\">Dr. Catherine M. Alder<\/a>\u00a0<a id=\"a8_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Edwards%2C+Lee+J\" data-id=\"a8\" data-db-target-for=\"a8\" aria-controls=\"a8\" aria-haspopup=\"true\">Lee J. Edwards<\/a>\u00a0<a id=\"a9_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=McKay%2C+Blandine+S+J\" data-id=\"a9\" data-db-target-for=\"a9\" aria-controls=\"a9\" aria-haspopup=\"true\">Dr. Blandine S. J. McKay<\/a>\u00a0<a id=\"a10_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Grayson%2C+Matthew+N\" data-id=\"a10\" data-db-target-for=\"a10\" aria-controls=\"a10\" aria-haspopup=\"true\">Dr. Matthew N. Grayson<\/a>\u00a0<a id=\"a11_Ctrl\" class=\"author-name accordion-tabbed__control\" role=\"button\" href=\"https:\/\/onlinelibrary.wiley.com\/action\/doSearch?ContribAuthorStored=Cresswell%2C+Alexander+J\" data-id=\"a11\" data-db-target-for=\"a11\" aria-controls=\"a11\" aria-haspopup=\"true\">Dr. Alexander J. Cresswell<\/a><\/p><p><strong>Link<\/strong><br \/><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/anie.202005294#.Xr2aciKIkvU.twitter\" target=\"_blank\" rel=\"noopener noreferrer\">https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/anie.202005294#.Xr2aciKIkvU.twitter<\/a><\/p><p>\u00a0<\/p>","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[478],"tags":[],"class_list":["post-24969","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-scientific-literature"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Photocatalytic \u03b1\u2010Tertiary Amine Synthesis via C\u2212H Alkylation of Unmasked Primary Amines<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" 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