{"id":79010,"date":"2024-10-15T15:13:39","date_gmt":"2024-10-15T06:13:39","guid":{"rendered":"https:\/\/www.waseda.jp\/inst\/research\/?p=79010"},"modified":"2024-11-15T15:13:56","modified_gmt":"2024-11-15T06:13:56","slug":"selective-c-n-bond-cleavage-in-unstrained-pyrrolidines-enabled-by-lewis-acid-and-photoredox-catalysis%ef%bc%88published-in-journal-of-the-american-chemical-society-october-2024%ef%bc%89","status":"publish","type":"post","link":"https:\/\/www.waseda.jp\/inst\/research\/news\/79010","title":{"rendered":"Selective C\u2013N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis\uff08Published in Journal of the American Chemical Society, October 2024\uff09"},"content":{"rendered":"\n\n\n\n\n\n\n\n\n
Journal Title
\n\/\u63b2\u8f09\u30b8\u30e3\u30fc\u30ca\u30eb\u540d<\/td>\n		Journal of the American Chemical Society<\/td>\n<\/tr>\n
Publication Year and Month
\n\/\u63b2\u8f09\u5e74\u6708<\/td>\n		October, 2024<\/td>\n<\/tr>\n
Paper Title
\n\/\u8ad6\u6587\u30bf\u30a4\u30c8\u30eb<\/td>\n		Selective C\u2013N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis<\/td>\n<\/tr>\n
DOI
\n\/\u8ad6\u6587DOI<\/td>\n		10.1021\/jacs.4c13210<\/a><\/td>\n<\/tr>\n
\u00a0Author of Waseda University
\n\/\u672c\u5b66\u306e\u8457\u8005<\/td>\n		AIDA, Kazuhiro(Student, Faculty of Science and Engineering, Graduate School of Advanced Science and Engineering):Lasr Author<\/span><\/td>\n<\/tr>\n
Related Websites
\n\/\u95a2\u9023Web<\/td>\n		–<\/td>\n<\/tr>\n
Abstract
\n\/\u6284\u9332<\/td>\n		Cleavage of inert C\u2013N bonds in unstrained azacycles such as pyrrolidine remains a formidable challenge in synthetic chemistry. To address this, we introduce an effective strategy for the reductive cleavage of the C\u2013N bond in\u00a0N<\/i>-benzoyl pyrrolidine, leveraging a combination of Lewis acid and photoredox catalysis. This method involves single-electron transfer to the amide, followed by site-selective cleavage at the C2\u2013N bond. Cyclic voltammetry and NMR studies demonstrated that the Lewis acid is crucial for promoting the single-electron transfer from the photoredox catalyst to the amide carbonyl group. This protocol is widely applicable to various pyrrolidine-containing molecules and enables inert C\u2013N bond cleavage including C\u2013C bond formation via intermolecular radical addition. Furthermore, the current protocol successfully converts pyrrolidines to aziridines, \u03b3-lactones, and tetrahydrofurans, showcasing its potential of the inert C\u2013N bond cleavage for expanding synthetic strategies.<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n","protected":false},"excerpt":{"rendered":"

Journal Title \/\u63b2\u8f09\u30b8\u30e3\u30fc\u30ca\u30eb\u540d Journal of the American Chemical Society Publication Year and Month \/\u63b2\u8f09\u5e74\u6708 October, 202 […]<\/p>\n","protected":false},"author":3,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[],"tags":[218,217],"class_list":["post-79010","post","type-post","status-publish","format-standard","hentry","tag-impact-en","tag-impact"],"acf":[],"_links":{"self":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/79010","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/comments?post=79010"}],"version-history":[{"count":1,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/79010\/revisions"}],"predecessor-version":[{"id":79012,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/posts\/79010\/revisions\/79012"}],"wp:attachment":[{"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/media?parent=79010"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/categories?post=79010"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.waseda.jp\/inst\/research\/wp-json\/wp\/v2\/tags?post=79010"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}