Bifunctional polymeric organocatalysts and their use in Morita-Baylis-Hillman reactions

ORGN 630

Cathy Kar-Wing Kwong1, Rui Huang2, Minjuan Zhang2, Min Shi, mshi@pub.sioc.ac.cn2, and Patrick H. Toy, phtoy@hku.hk1. (1) Department of Chemistry, University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong, (2) School of Chemistry & Pharmaceutics, East China University of Science and Technology, 130 Meilong Road, Shanghai, China
A series of soluble, non-cross-linked polystyrene-supported triphenylphosphine and 4-dimethylaminopyridine reagents have been prepared. Some of these polymeric reagents contain 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 indicates that the hydroxyl groups can participate in the reactions and accelerate product formation. In the cases examined, phenol groups are more effective than alkyl alcohol groups in catalyzing the reactions. This is one of the first reports of the synthesis and use of non-natural, bifunctional polymeric reagents in the context of organic synthesis, where both functional groups can cooperatively participate in the catalysis of reactions.