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An Improved Cu-Based Catalyst System for the Reactions of Alcohols with Aryl Halides

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Ryan A. Altman, Alexandr Shafir, Alice Choi, Phillip A. Lichtor, and Stephen L. Buchwald*

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 sbuchwal@mit.edu

J. Org. Chem., 2008, 73 (1), pp 284–286

DOI: 10.1021/jo702024p

Publication Date (Web): November 29, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The use of 3,4,7,8-tetramethyl-1,10-phenanthroline (Me₄Phen) as a ligand improves the Cu-catalyzed cross-coupling reactions of aryl iodides and bromides with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols. Most importantly, by employing this catalyst system, the need to use an excessive quantity of the alcohol coupling partner is alleviated. The relatively mild conditions, short reaction times, and moderately low catalyst loading allow for a wide array of functional groups to be tolerated on both the electrophilic and nucleophilic coupling partners.

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