Selective Arylation and Vinylation at the α Position of Vinylarenes
Zhou, Jianrong Steve
Date of Issue2013
School of Physical and Mathematical Sciences
In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion.
DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
Chemistry - A European Journal
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.