Issue 24, 2021

Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp3)–H bond cleavage

Abstract

A three-component photoredox 1,2-alkylamination of styrenes involving functionalization of C(sp3)–H bonds in alkyl halides instead of functionalization of C-halogen bonds is disclosed. A variety of commercialized C(sp3)–H alkanes, including dichloromethane, acetonitrile, and acetone, used as alkyl radical precursors and solvents, were compatible with this methodology. The mechanistic study shows that alkyl radicals are generated by hydrogen atom transfer (HAT) between aryl radicals and alkyl halides.

Graphical abstract: Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp3)–H bond cleavage

Supplementary files

Article information

Article type
Research Article
Submitted
23 Aug 2021
Accepted
29 Oct 2021
First published
03 Nov 2021

Org. Chem. Front., 2021,8, 7009-7014

Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp3)–H bond cleavage

J. Huang, Y. Liang, X. Ouyang, Y. Xiao, J. Qin, R. Song and J. Li, Org. Chem. Front., 2021, 8, 7009 DOI: 10.1039/D1QO01263K

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