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Palladium-Catalyzed Carbonylation of Aryl Tosylates and Mesylates

Rachel H. Munday, Joseph R. Martinelli and Stephen L. Buchwald*

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

R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc., 2008, 130, 2754-2755.

DOI: 10.1021/ja711449e (free Supporting Information)


Abstract

A system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand catalyzes the carbonylation of aryl tosylates and mesylates to form esters under atmospheric CO pressure and temperatures of 80-110C. A broad substrate scope allows carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance.

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Key Words

Arenes


ID: J48-Y2008-0530