Issue 8, 2012

Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles

Abstract

Aryl and alkenylgold(I) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.

Graphical abstract: Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2011
Accepted
06 Dec 2011
First published
07 Dec 2011

Org. Biomol. Chem., 2012,10, 1686-1694

Palladium-catalyzed cross-coupling reactions of organogold(I) phosphanes with allylic electrophiles

M. Peña-López, M. Ayán-Varela, L. A. Sarandeses and J. P. Sestelo, Org. Biomol. Chem., 2012, 10, 1686 DOI: 10.1039/C2OB06788A

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