Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid

J Org Chem. 2012 Oct 5;77(19):8678-88. doi: 10.1021/jo301642v. Epub 2012 Sep 20.

Abstract

The use of bis-boronic acid for the direct synthesis of boronic acids has greatly facilitated the two-step, one-pot borylation/Suzuki cross-coupling reaction between aryl and heteroaryl halides. With use of Buchwald's second-generation XPhos preformed catalyst, high yields of cross-coupled products were obtained for most substrates. The method also allows an efficient two-step, one-pot synthesis, providing access to three distinct cross-coupled products after column chromatography. The method also provides a rapid and convenient route to teraryl compounds.

Publication types

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

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Chromatography, Liquid / methods
  • Cross-Linking Reagents / chemical synthesis*
  • Cross-Linking Reagents / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Boronic Acids
  • Cross-Linking Reagents
  • Hydrocarbons, Halogenated
  • Palladium