Copper-Catalyzed Coupling of Aryl Iodides with Aliphatic Alcohols

Martina Wolter, Gero Nordmann, Gabriel E. Job, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
Org. Lett., 2002, 4 (6), pp 973–976
DOI: 10.1021/ol025548k
Publication Date (Web): February 22, 2002
Copyright © 2002 American Chemical Society
*

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

Abstract Image

A simple and mild method for the coupling of aryl iodides and aliphatic alcohols that does not require the use of alkoxide bases is described. The reactions can be performed in neat alcohol. For more precious alcohols, the etherification was carried out in toluene as solvent using 2 equiv of alcohol. Additionally, the cross-coupling of an optically active benzylic alcohol with an unactivated aryl halide was demonstrated to proceed with complete retention of configuration.

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History

  • Published In Issue March 21, 2002
  • Received January 12, 2002

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