Differentially protected benzenediboronic acids: divalent cross-coupling modules for the efficient synthesis of boron-substituted oligoarenes

Org Lett. 2008 Feb 7;10(3):377-80. doi: 10.1021/ol702420x. Epub 2008 Jan 10.

Abstract

On the basis of the boron-masking strategy, new divalent cross-coupling modules have been designed for the efficient synthesis of boron-substituted oligoarenes. The modules, i.e., monoprotected o-, m-, and p-benzenediboronic acid derivatives, undergo highly selective Suzuki-Miyaura coupling with sp2 iodides, bromides, chlorides, and triflates, affording coupling products in which the protected boronyl groups are left intact.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Hydrocarbons, Halogenated / chemistry
  • Mesylates / chemistry
  • Models, Molecular*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Boron Compounds
  • Boronic Acids
  • Hydrocarbons, Halogenated
  • Mesylates
  • benzeneboronic acid