Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho-quinone catalyst

Org Lett. 2015 Mar 20;17(6):1469-72. doi: 10.1021/acs.orglett.5b00351. Epub 2015 Mar 11.

Abstract

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of α-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Imines / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Quinones / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Imines
  • Quinones