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Carbonylation of Aryl Chlorides with Oxygen Nucleophiles at Atmospheric Pressure. Preparation of Phenyl Esters as Acyl Transfer Agents and the Direct Preparation of Alkyl Esters and Carboxylic Acids

Donald A. Watson, Xuexiang Fan and Stephen L. Buchwald*

*Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

D. A. Watson, X. Fan, S. L. Buchwald, J. Org. Chem., 2008, 73, 7096-7101.

DOI: 10.1021/jo800907e (free Supporting Information)



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Abstract

A mild, functional group tolerant palladium-catalyzed carbonylation of aryl chlorides using atmospheric pressure of carbon monoxide allows the preparation of phenyl esters, alkyl esters and carboxylic acids. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions.

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Key Words

Benzoic Acid Derivatives, Transesterification


ID: J42-Y2008-2500