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

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

Organic & biomolecular chemistry (2012-01-24)
Miguel Peña-López, Miguel Ayán-Varela, Luis A Sarandeses, José Pérez Sestelo
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Geranyl bromide, 95%
Sigma-Aldrich
Cinnamyl chloride, 95%
Sigma-Aldrich
Geranyl chloride, 95%