One-pot Negishi cross-coupling reactions of in situ generated zinc reagents with aryl chlorides, bromides, and triflates

J Org Chem. 2008 Sep 19;73(18):7380-2. doi: 10.1021/jo801063c. Epub 2008 Aug 12.

Abstract

In situ generated aryl, heteroaryl, alkyl, or benzylic polyfunctional zinc reagents obtained by the addition of zinc and LiCl to the corresponding organic iodides undergo smooth Pd(0)-catalyzed cross-coupling reactions with aryl bromides, chlorides, and triflates in the presence of PEPPSI as a catalyst. This procedure avoids the manipulation of water and air-sensitive organozinc reagents and produces cross-coupling products in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Brominated / chemistry*
  • Hydrocarbons, Chlorinated / chemistry*
  • Lithium Chloride / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Hydrocarbons, Brominated
  • Hydrocarbons, Chlorinated
  • Mesylates
  • Organometallic Compounds
  • Lithium Chloride
  • Zinc
  • trifluoromethanesulfonic acid