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Article

An Extremely Active Catalyst for the Negishi Cross-Coupling Reaction

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Jacqueline E. Milne and Stephen L. Buchwald*

Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2004, 126 (40), pp 13028–13032

DOI: 10.1021/ja0474493

Publication Date (Web): September 15, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sbuchwal@mit.edu

Abstract

A new catalyst system for the Pd-catalyzed cross-coupling of organozinc reagents with aryl halides (Negishi coupling) has been developed. This system permits efficient preparation of hindered biaryls (tri- and tetra-ortho-substituted), functions effectively at low levels of catalyst, and tolerates a wide range of functional groups and heterocyclic substrates. A systematic study of ligand structure was performed and was correlated with catalyst activity.

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Published In Issue October 13, 2004
Received April 30, 2004

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Article

An Extremely Active Catalyst for the Negishi Cross-Coupling Reaction