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Bifunctional Polymeric Organocatalysts and Their Application in the Cooperative Catalysis of Morita–Baylis–Hillman Reactions
Author(s) -
Kwong Cathy KarWing,
Huang Rui,
Zhang Minjuan,
Shi Min,
Toy Patrick H.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601197
Subject(s) - bifunctional , reagent , chemistry , organic chemistry , alkyl , alcohol , phenol , catalysis , organocatalysis , polystyrene , combinatorial chemistry , polymer , enantioselective synthesis
A series of soluble, non‐cross‐linked polystyrene‐supported triphenylphosphane 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.