Palladium-Catalyzed Aryl−Aryl Cross-Coupling Reaction Using ortho-Substituted Arylindium Reagents†

Miguel A. Pena, José Pérez Sestelo,* and Luis A. Sarandeses*;
Departamento de Qumica Fundamental, Universidade da Corua, E-15071 A Corua, Spain
J. Org. Chem., 2007, 72 (4), pp 1271–1275
DOI: 10.1021/jo062148s
Publication Date (Web): January 25, 2007
Copyright © 2007 American Chemical Society
*

 Corresponding authors. Tel.:  34-981-167-000. Fax:  34-981-167-065.

, qfsarand@udc.es, ; , sestelo@udc.es

Abstract

Abstract Image

A range of biaryl compounds (aryl−aryl, aryl−heteroaryl, and heteroaryl−heteroaryl) can be efficiently prepared by a palladium-catalyzed cross-coupling reaction between ortho-substituted triarylindium reagents and aryl halides. The triarylindium reagents are prepared by directed ortho-lithiation and transmetallation to indium from the corresponding benzene derivatives using various directed metallation groups (DMGs). The reaction proceeds smoothly in high yields and short reaction times with high atom economy (the three aryl groups attached to indium are efficiently transferred).

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History

  • Published In Issue February 16, 2007
  • Received October 17, 2006

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