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Palladium-Catalyzed Allylic Acyloxylation of Terminal Alkenes in the Presence of a Base

Emilie Thiery, Chahinez Aouf, Julien Belloy, Dominique Harakat, Jean Le Bras and Jacques Muzart

*Institut de Chimie Moléculaire de Reims, UMR 6229 CNRS-Université de Reims Champagne-Ardenne, UFR des Sciences exactes et naturelles, BP 1039, 51687 REIMS Cedex 2, France, Email:

E. Thiery, C. Aouf, J. Belloy, D. Harakat, J. Le Bras, J. Muzart, J. Org. Chem., 2010, 75, 1771-1774.

DOI: 10.1021/jo902587u

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The presence of a base strongly improves the efficiency and the selectivity of the Pd-catalyzed oxidation of terminal alkenes in carboxylic acids. The methodology is particularly well adapted for the oxidation of homoallylic alcohols, for which the resulting acyloxylated products are obtained selectively as E-isomers in good yields.

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Key Words

Esters, Allylic Alcohols, Benzoquinone

ID: J42-Y2010-0630