Direct oxidative arylation of aryl C - H bonds with aryl boronic acids via pd catalysis directed by the N,N-dimethylaminomethyl group

Chem Asian J. 2015 Apr;10(4):840-3. doi: 10.1002/asia.201403292. Epub 2015 Jan 21.

Abstract

Biaryl skeletons were directly constructed via palladium-catalyzed ortho-arylation of N,N-dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open-flask conditions. The N,N-dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho-monoarylated or -diarylated arenes in moderate to good yields under mild conditions.

Keywords: CH activation; N,N-dimethylbenzylamine; biaryls; boronic acid; oxidative coupling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Hydrocarbons / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Boronic Acids
  • Hydrocarbons
  • Palladium