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

Rachel Lerebours, Alejandra Camacho-Soto and Christian Wolf*

*Department of Chemistry, Georgetown University, Washington, D.C. 20057, Email: cw27georgetown.edu

R. Lerebours, A. Camacho-Soto, C. Wolf, J. Org. Chem., 2005, 70, 8601-8604.

DOI: 10.1021/jo051257o (free Supporting Information)


Abstract

Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with organostannanes provides a useful alternative to Friedel-Crafts acylations for the synthesis of ketones. A range of ketones are obtained in high yield using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II) dichloride as precatalyst. The catalyst tolerates various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes.

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Key Words

Acylation, Organostannanes Stille Coupling


ID: J42-Y2005-1650