Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation

Org Lett. 2013 Sep 6;15(17):4358-61. doi: 10.1021/ol401858k. Epub 2013 Aug 19.

Abstract

Redox-neutral formation of C-P bonds in the α-position of amines was achieved via a process that features a combination of an oxidative α-C-H bond functionalization and a reductive N-alkylation. Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to α-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkylation
  • Amines / chemistry*
  • Benzoic Acid / chemistry*
  • Catalysis
  • Molecular Structure
  • Oxidation-Reduction
  • Phosphines / chemistry

Substances

  • Aldehydes
  • Amines
  • Phosphines
  • Benzoic Acid
  • phosphine