Bifunctional polymeric organocatalysts and their application in the cooperative catalysis of Morita-Baylis-Hillman reactions

Abstract

A series of soluble, noncross-linked polystyrene-supported tri-phenylphosphane and 4-dimethylaminopyridine reagents were prepared. Some of these polymeric reagents contained either alkyl alcohol or phenol groups on the polymer backbone. The use of these materials as organocatalysts in a range of Morita-Baylis-Hillman reactions indicated that hydroxyl groups could participate in the reactions and accelerate product formation. In the cases examined, phenol groups were more effective than alkyl alcohol groups for catalyzing the reactions. This article is one of the first reports of the synthesis and use of non-natural, bifunctional polymeric reagents for use in organic synthesis in which both functional groups can cooperatively participate in the catalysis of reactions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.