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Stereoselective Synthesis of Tetrahydrofurans via the Palladium-Catalyzed Reaction of Aryl Bromides with γ-Hydroxy Alkenes: Evidence for an Unusual Intramolecular Olefin Insertion into a Pd(Ar)(OR) Intermediate

John P. Wolfe* and Michael A. Rossi

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, Email:

J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc., 2004, 126, 1620-1621.

DOI: 10.1021/ja0394838


A new, stereoselective, palladium-catalyzed method for the synthesis of substituted tetrahydrofurans from γ-hydroxy alkenes and aryl bromides forms both a C-C and a C-O bond with diastereoselectivities of up to >20:1. The reactions probably proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) intermediate.

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Key Words

Tetrahydrofurans, Arenes

ID: J48-Y2004-1380