879549-74-3Relevant academic research and scientific papers
Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes
Wright, Joseph A.,Gaunt, Matthew J.,Spencer, Jonathan B.
, p. 949 - 955 (2007/10/03)
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.
