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Palladium-Catalyzed Olefin Dioxygenation

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Yang Li, Datong Song,* and Vy M. Dong*;

Davenport Chemical Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, CANADA

J. Am. Chem. Soc., 2008, 130 (10), pp 2962–2964

DOI: 10.1021/ja711029u

Publication Date (Web): February 19, 2008

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and PhI(OAc)₂ as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An ¹⁸O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.

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