Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes

Abstract

Allylation of alpha,beta-unsaturated aldehydes and cyclic ketones promoted by Pd/In transmetallation processes has been Studied. The unsaturated aldehydes underwent regioselective 1,2-addition to afford secondary homoally alcohols. The reactions have been performed using Pd(OAc)(2)/PPh(3) as catalytic system and metallic indium affording the products in good yields. The same transformation with unsaturated ketones proved to be less efficient, while saturated cyclic ketones delivered generally excellent yields in the presence of Cul. In these latter processes the presence of a distal heteroatom influences the reaction rate.