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Palladium-Catalyzed Chemoselective Cross-Coupling of Acyl Chlorides and Organostannanes

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Rachel Lerebours, Alejandra Camacho-Soto, and Christian Wolf*

Department of Chemistry, Georgetown University, Washington, D.C. 20057 %cw27@georgetown.edu

J. Org. Chem., 2005, 70 (21), pp 8601–8604

DOI: 10.1021/jo051257o

Publication Date (Web): September 17, 2005

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

Abstract

Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with aryl-, heteroaryl-, and alkynylstannanes proceeds in up to 98% yield using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II) dichloride as the precatalyst. Various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes bearing phosphinous acid or dialkylchlorophosphine ligands are tolerated. This procedure allows convenient ketone formation and eliminates inherent limitations of Friedel−Crafts acylations such as substituent-directing effects and typical reactivity requirements of Lewis acid-catalyzed electrophilic aromatic substitutions.

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Published In Issue October 14, 2005
Received June 18, 2005

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Palladium-Catalyzed Chemoselective Cross-Coupling of Acyl Chlorides and Organostannanes