Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates

J Org Chem. 2008 Mar 21;73(6):2052-7. doi: 10.1021/jo800183q. Epub 2008 Feb 20.

Abstract

We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

Publication types

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

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry*
  • Borates / chemistry*
  • Catalysis
  • Chlorobenzenes
  • Hydrocarbons, Halogenated / chemistry
  • Methylation
  • Palladium

Substances

  • Amines
  • Benzene Derivatives
  • Borates
  • Chlorobenzenes
  • Hydrocarbons, Halogenated
  • Palladium