{"id":25012,"date":"2019-02-08T17:18:53","date_gmt":"2019-02-09T00:18:53","guid":{"rendered":"https:\/\/hepatochem.com\/primary-%ce%b1-tertiary-amine-synthesis-via-%ce%b1-c-h-functionalization\/"},"modified":"2019-02-08T17:18:53","modified_gmt":"2019-02-09T00:18:53","slug":"primary-%ce%b1-tertiary-amine-synthesis-via-%ce%b1-c-h-functionalization","status":"publish","type":"post","link":"https:\/\/hepatochem.com\/fr\/primary-%ce%b1-tertiary-amine-synthesis-via-%ce%b1-c-h-functionalization\/","title":{"rendered":"Primary \u03b1-tertiary amine synthesis via \u03b1-C\u2013H functionalization"},"content":{"rendered":"<p><!DOCTYPE html PUBLIC \"-\/\/W3C\/\/DTD HTML 4.0 Transitional\/\/EN\" \"http:\/\/www.w3.org\/TR\/REC-html40\/loose.dtd\"><br \/>\n<html><body><strong>Abstract<\/strong><\/p>\n<p>A quinone-mediated general synthetic platform for the construction of primary \u03b1-tertiary amines from abundant primary \u03b1-branched amine starting materials is described. This procedure pivots on the efficient<em>in <img loading=\"lazy\" decoding=\"async\" class=\"alignright size-full wp-image-8346\" src=\"https:\/\/hepatochem.com\/wp-content\/uploads\/2020\/09\/Screen-Shot-2020-09-01-at-8.22.45-PM.png\" alt=\"\" width=\"265\" height=\"196\">situ<\/em>generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles,<em>via<\/em>a nucleophilic \u03b1-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.<\/p>\n<p><strong>Authors:<\/strong> <span class=\"article__author-link\"><a href=\"https:\/\/pubs.rsc.org\/en\/results?searchtext=Author%3ADhananjayan%20Vasu\">Dhananjayan Vasu<\/a>,<span class=\"orcid ver-b\"><a title=\"Select to open ORCID record (orcid.org\/0000-0001-7597-3710) in a new window\" href=\"https:\/\/orcid.org\/0000-0001-7597-3710\" target=\"_blank\" rel=\"noopener noreferrer\"><img decoding=\"async\" src=\"https:\/\/www.rsc-cdn.org\/pubs-core\/2020.0.188\/content\/NewImages\/orcid_16x16.png\" alt=\"ORCID logo\"><\/a><\/span><sup><i>a<\/i><\/sup><\/span><span class=\"article__author-link\"><a href=\"https:\/\/pubs.rsc.org\/en\/results?searchtext=Author%3AAngel%20L.%20Fuentes%20de%20Arriba\">Angel L. Fuentes de Arriba<\/a>,<span class=\"orcid ver-b\"><a title=\"Select to open ORCID record (orcid.org\/0000-0001-7424-8146) in a new window\" href=\"https:\/\/orcid.org\/0000-0001-7424-8146\" target=\"_blank\" rel=\"noopener noreferrer\"><img decoding=\"async\" src=\"https:\/\/www.rsc-cdn.org\/pubs-core\/2020.0.188\/content\/NewImages\/orcid_16x16.png\" alt=\"ORCID logo\"><\/a><\/span><sup><i>a<\/i><\/sup><\/span><span class=\"article__author-link\"><a href=\"https:\/\/pubs.rsc.org\/en\/results?searchtext=Author%3AJamie%20A.%20Leitch\">Jamie A. Leitch<\/a>,<span class=\"orcid ver-b\"><a title=\"Select to open ORCID record (orcid.org\/0000-0001-6997-184X) in a new window\" href=\"https:\/\/orcid.org\/0000-0001-6997-184X\" target=\"_blank\" rel=\"noopener noreferrer\"><img decoding=\"async\" src=\"https:\/\/www.rsc-cdn.org\/pubs-core\/2020.0.188\/content\/NewImages\/orcid_16x16.png\" alt=\"ORCID logo\"><\/a><\/span><sup><i>a<\/i><\/sup><\/span><span class=\"article__author-link\"><a href=\"https:\/\/pubs.rsc.org\/en\/results?searchtext=Author%3AAntoine%20de%20Gombert\">Antoine de Gombert<\/a><sup><i>a<\/i><\/sup>and<\/span><span class=\"article__author-link\"><a href=\"https:\/\/pubs.rsc.org\/en\/results?searchtext=Author%3ADarren%20J.%20Dixon\">Darren J. Dixon<\/a><span class=\"orcid ver-b\"><a title=\"Select to open ORCID record (orcid.org\/0000-0003-2456-5236) in a new window\" href=\"https:\/\/orcid.org\/0000-0003-2456-5236\" target=\"_blank\" rel=\"noopener noreferrer\"><img decoding=\"async\" src=\"https:\/\/www.rsc-cdn.org\/pubs-core\/2020.0.188\/content\/NewImages\/orcid_16x16.png\" alt=\"ORCID logo\"><\/a><\/span>*<sup><i>a<\/i><\/sup><\/span><\/p>\n<p><strong>Link: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2019\/sc\/c8sc05164j#!divAbstract\" target=\"_blank\" rel=\"noopener noreferrer\">https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2019\/sc\/c8sc05164j#!divAbstract<\/a><\/body><\/html><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Abstract A quinone-mediated general synthetic platform for the construction of primary \u03b1-tertiary amines from abundant primary \u03b1-branched amine starting materials is described. This procedure pivots on the efficientin situgeneration of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":25013,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"","_et_pb_old_content":"","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[489],"tags":[],"class_list":["post-25012","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 v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Primary \u03b1-tertiary amine synthesis via \u03b1-C\u2013H functionalization<\/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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