Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes

Jospeh A. Wright, Matthew J. Gaunt, Jonathan B. Spencer

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83 Citations (Scopus)

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 η4-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.
Original languageEnglish
Pages (from-to)949-955
Number of pages7
JournalChemistry - A European Journal
Volume12
Issue number3
Early online date5 Jan 2006
DOIs
Publication statusPublished - 11 Jan 2006

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