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Chemistry. 2006 Jan 11;12(3):949-55.

Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes.

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1
University Chemical Laboratories, University of Cambridge, UK.

Abstract

The Wacker reaction is one of the longest known palladium-catalysed organic transformations, and in the vast majority of cases proceeds with Markovnikov regioselectivity. Palladium(II)-mediated oxidation of styrenes was examined and in the absence of reoxidants was found to proceed in an anti-Markovnikov sense, giving aldehydes. Studies on the mechanism of this unusual transformation were carried out, and indicate the possible involvement of a eta(4)-palladium-styrene complex. With a heteropolyacid as the terminal oxidant, oxidation of styrene to give the anti-Markovnikov aldehyde as the major product was found to be catalytic.

PMID:
16144020
DOI:
10.1002/chem.200400644

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