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Synfacts 2011(9): 1025-1025  
DOI: 10.1055/s-0030-1260893
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Suzuki-Miyaura Coupling in Water Using an NHC-Pd Polymer

Contributor(s):Yasuhiro Uozumi, Takao Osako
B. Karimi*, P. F. Akhavan
Institute for Advanced Studies in Basic Sciences, Gava Zang, Iran
A Novel Water-Soluble NHC-Pd Polymer: An Efficient and Recyclable Catalyst for the Suzuki Coupling of Aryl Chlorides in Water at Room Temperature
Chem. Commun.  2011,  47:  7686-7688  
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Publication History

Publication Date:
19 August 2011 (online)

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Key words

water - NHC-Pd polymer - Suzuki-Miyaura coupling - aryl halides - arylboronic acids

Significance

A water-soluble NHC-Pd polymer 3 was prepared by the reaction of 1 with TEG-Br in the presence of NaH followed by treatment with Pd(OAc)2 (eq. 1). The NHC-Pd polymer 3 catalyzed the Suzuki-Miyaura coupling of aryl bromides or aryl chlorides with arylboronic acids in water to give the corresponding biaryls in 69-93% yield (21 examples, eq. 2).

Comment

GPC analysis revealed that the average molecular weight of the NHC-Pd polymer 3 was around 107000 Da. After the reaction of 4-chlorobenzaldehyde with phenylboronic acid, the product was extracted with n-hexane and the resulting aqueous solution containing 3 was subjected to the recycling runs.

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