Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides

Org Lett. 2007 Apr 12;9(8):1597-600. doi: 10.1021/ol070543e. Epub 2007 Mar 17.

Abstract

[reaction: see text] The Suzuki-Miyaura cross-coupling reaction of N,N-dialkylaminomethyltrifluoroborates with aryl halides allows the construction of an aminomethyl aryl linkage through a disconnection based on dissonant reactivity patterns. A variety of these aminomethyltrifluoroborate substrates were prepared in good to excellent yields and then shown to cross-couple with equal facility to both electron-rich and electron-poor aryl halides as well as to a variety of heteroaromatic bromides.

Publication types

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

MeSH terms

  • Amination
  • Borates / chemistry*
  • Bromides / chemistry*
  • Cross-Linking Reagents / chemistry*
  • Methylation
  • Molecular Structure
  • Nitrogen Compounds / chemistry
  • Organic Chemicals / chemistry*
  • Potassium / chemistry*

Substances

  • Borates
  • Bromides
  • Cross-Linking Reagents
  • Nitrogen Compounds
  • Organic Chemicals
  • Potassium