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Organic & biomolecular chemistry

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


PMID 22266785

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.

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