Metal-free oxidative olefination of primary amines with benzylic C–H bonds through direct deamination and C–H bond activation?

Organic & Biomolecular Chemistry Pub Date: 2014-07-08 DOI: 10.1039/C4OB01025F

Abstract

An oxidative olefination reaction between aliphatic primary amines and benzylic sp3 C–H bonds has been achieved using N-bromosuccinimide as catalyst and tert-butyl hydroperoxide as oxidant. The olefination proceeds under mild metal-free conditions through direct deamination and benzylic C–H bond activation, and provides easy access to biologically active 2-styrylquinolines with (E)-configuration.

Graphical abstract: Metal-free oxidative olefination of primary amines with benzylic C–H bonds through direct deamination and C–H bond activation
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