Chemoselective Organocatalytic Aerobic Oxidation of Primary Amines to Secondary Imines

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2012 May 19

PMID 22594886

Citations 18

Authors

Alison E Wendlandt

Shannon S Stahl

Affiliations

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Abstract

Biomimetic aerobic oxidation of primary benzylic amines has been achieved by using a quinone catalyst. Excellent selectivity is observed for primary, unbranched benzylic amines relative to secondary/tertiary amines, branched benzylic amines, and aliphatic amines. The exquisite selectivity for benzylic amines enables oxidative self-sorting within dynamic mixtures of amines and imines to afford high yields of cross-coupled imine products.

Citing Articles

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