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Synfacts 2006(11): 1179-1179  
DOI: 10.1055/s-2006-949409
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

PS-PEG-Supported Aryldicyclohexylphosphine Ligand for Pd-Catalyzed Suzuki Coupling

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
K. Glegoa, E. Framery*, K. M. Pietrusiewicz, D. Sinou*
Université Claude Bernard Lyon 1, Villeurbanne, France and Maria Curie-Sklodowska University, Lublin, Poland
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

Polymer-supported aryldicyclohexyl­phosphines were prepared and used as ligands in the palladium-catalyzed Suzuki-Miyaura coupling reaction. The polymer-supported aryldicyclohexyl­phosphines 3 were prepared by the condensation of the carboxylic acid 1 with polystyrene carrying an amino group (2a) or polystyrene-poly(ethylene glycol) copolymer (PS-PEG) with an amino group (2b) in the presence of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole (HOBt) (eq. 1). The Suzuki-Miyaura coupling reaction of aryl chlorides with arylboronic acids took place in the presence of Pd(OAc)2 and the ligands 3 to give the biaryls in 30-91% yield and 0-96% yield (eq. 2). The catalyst derived from Pd(OAc)2 and ligand 3b was reused three times without significant loss of activity (91-100% yield).