Organic Letters 2001-03-22

Palladium-catalyzed tandem bis-allylation of isocyanates.

N Solin, S Narayan, K J Szabó

Index: Org. Lett. 3(6) , 909-12, (2001)

Full Text: HTML

Abstract

A tandem bis-allylation of p-toluenesulfonyl isocyanate can be achieved by palladium-catalyzed three-component coupling reaction with allylstannanes and allyl chlorides. A high level of regioselectivity can be obtained by the appropriate choice of the allylic substituents. The reaction mechanism and the regiochemistry of the reaction can be explained by formation of an amphoteric bis-allylpalladium intermediate. This bis-allylpalladium intermediate undergoes an initial electrophilic attack on one of the allyl moieties followed by a nucleophilic attack on the other.