Synthesis of diarylmethanes via metal-free reductive cross-coupling of diarylborinic acids with tosyl hydrazones

J Org Chem. 2012 Dec 7;77(23):10991-5. doi: 10.1021/jo302207b. Epub 2012 Nov 20.

Abstract

This paper describes a practical and efficient procedure that takes advantage of diarylborinic acids as a cost-effective alternative to arylboronic acids for synthesis of diarylmethanes through metal-free reductive cross-coupling with N-tosylhydrazones of aromatic aldehydes and ketones. The procedure tolerates hydroxyl, halide, amine, and allyl functionality, complementary to the transition-metal catalyzed cross-coupling techniques.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Hydrazones / chemistry*
  • Ketones / chemistry*
  • Metals / chemistry*
  • Molecular Structure
  • Tosyl Compounds / chemistry*

Substances

  • Aldehydes
  • Boronic Acids
  • Cross-Linking Reagents
  • Hydrazones
  • Ketones
  • Metals
  • Tosyl Compounds