文章基本信息

标题：The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes
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作者：Yu-Qing Guan ; Xiang-Ting Min ; Gu-Cheng He 等
期刊名称：iScience
印刷版ISSN：2589-0042
出版年度：2021
卷号：24
期号：9
页码：1-31
DOI：10.1016/j.isci.2021.102969
语种：English
出版社：Elsevier
摘要：SummaryRitter reaction has been recognized as an elegant strategy to construct the C−N bond. Its key feature is forming the carbocation for nucleophilic attack by nitriles. Herein, we report a complementary visible-light-induced three-component Ritter reaction of alkenes, nitriles, andα-bromo nitriles/esters, thereby providing mild and rapid access to variousγ-amino nitriles/acids. Mechanistic studies indicated that traceless fluoride relay, transforming KF into imidoyl fluoride intermediate, is critical for the efficient reaction switch from atom transfer radical addition (ATRA) to the Ritter reaction. This approach to amino-alkylation of alkenes is chemoselective and operationally simple.Graphical abstractDisplay OmittedHighlights•Using light irradiation to promote amino-alkylation of alkenes•Using KF to facilitate three-component Ritter reaction•Access functionalized amides under mild conditionsChemistry; Organic chemistry; Organic synthesis