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Regioselective Thiocarbonylation of Vinyl Arenes
Vera Hirschbeck1, Paul H Gehrtz1, Ivana Fleischer1
1Institute of Organic Chemistry, University of Regensburg , Universitätsstraße 31, D-93053 Regensburg, Germany.
Abstract:
A palladium-catalyzed thiocarbonylation of styrene derivatives is reported for the first time. The combination of thiols as nucleophiles and a bidentate ligand ensures a unique reaction outcome with high regioselectivity toward the more valuable branched isomer and new reactivity. The ambient reaction conditions (temperature, catalyst loading) and the use of a CO surrogate render this transformation a useful method for the synthesis of thioesters from available feedstock. Various functional groups on arene and thiol substituents are tolerated by the system. Notably, challenging ortho-substituted styrenes are converted with unprecedentedly high regioselectivity.
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