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

Peña-López, M.; Ayán-Varela, M.; Sarandeses, L. A.; Pérez Sestelo, J.


Org. Biomol. Chem. 2012, 10, 16861694 (DOI: 10.1039/c2ob06788a).

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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.