Organic Letters 2008-10-02

Palladium-catalyzed C-allylation of benzoins and an NHC-catalyzed three component coupling derived thereof: compatibility of NHC- and Pd-catalysts.

Raphaël Lebeuf, Keiichi Hirano, Frank Glorius

Index: Org. Lett. 10 , 4243-4246, (2008)

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Abstract

A large range of benzoins was successfully applied as C-nucleophiles in the palladium-catalyzed allylic alkylation with several allyl acetates, resulting in functionalized tertiary homoallylic alcohols. A number of unsymmetrical benzoins can be coupled with high levels of regio- and chemoselectivity. Finally, the challenging compatibility of free N-heterocyclic carbenes with a palladium catalyst has been utilized in a number of metal- and organocatalyzed three-component coupling reactions.