Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features of this protocol are easy-to-obtain starting materials, a wide range of substrates, and functional group tolerance as well as high atom economy, thus offering a strategy...

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Published inJournal of organic chemistry Vol. 89; no. 12; pp. 8342 - 8356
Main Authors Ren, Man, Yu, Shengjiao, Li, Xuefeng, Yuan, Wenlong, Lu, Ji, Xiong, Ying, Liu, Hongliang, Wang, Jun, Wei, Jun
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.06.2024
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Summary:A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features of this protocol are easy-to-obtain starting materials, a wide range of substrates, and functional group tolerance as well as high atom economy, thus offering a strategy to access a variety of gem-difluorohomoallyl amines, which are extensively distributed in pharmaceuticals and bioactive agents, with excellent chemoselectivity. The primary products can be further transformed to a diversity of 2-fluorinated pyrroline compounds.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00084