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Palladium-Catalyzed Coupling of Allylic Acetates with Aryl- and Vinylstannanes

L. Del Valle, J. K. Stille and L. S. Hegedus*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523

L. Del Valle, J. K. Stille, L. S. Hegedus, J. Org. Chem, 1990, 55, 3019-3023.

DOI: 10.1021/jo00297a014


The palladium-catalyzed reaction of allyl acetates with aryl- and vinyltin reagents gave good yields of cross-coupled products. The reaction was mild and tolerant of functionality (-CO2R, -OH, -OSiR3, -OMe) in the tin reagent. Inversion of stereochemistry at the acetate center was observed, with retention of the geometry of the olefin of the allyl group and with exclusive coupling at the primary position. Retention of geometry of the olefin in the vinyltin reagents was also observed.

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proposed mechanism

Key Words

Stille Coupling, Palladium Catalysis, Allyl Acetates, Aryltin Reagents, Vinyltin Reagents, Allyls, Arenes, Vinyls

ID: J42-Y1990-090