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Synlett 2008(4): 611-613  
DOI: 10.1055/s-2008-1032081
LETTER
© Georg Thieme Verlag Stuttgart · New York

Sustainable Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)2 Immobilized on Reversed-Phase Alumina

Hisahiro Hagiwara*a, Keon Hyeok Koa, Takashi Hoshib, Toshio Suzukib
a Graduate School of Science and Technology, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan
Fax: +81(25)2627368; e-Mail: hagiwara@gs.niigata-u.ac.jp;
b Faculty of Engineering, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan
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Publication History

Received 22 November 2007
Publication Date:
12 February 2008 (online)

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Abstract

Employing Pd(OAc)2 immobilized on amorphous N,N-diethylaminopropyl alumina, Suzuki-Miyaura coupling of aryl halide with arylboronic acid was realized in 50% aqueous ethanol at room temperature, which enabled repeated use up to four times in 96% average yield and achieved a turnover number of 15 000.

Key words

arylations - boron - cross-coupling - heterogeneous catalysis - palladium - supported catalysis

    References and Notes

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7

Typical Experimental Procedure: To a stirred solution of 4-bromoacetophenone (96 mg, 0.48 mmol), 4-acetylphen-ylboronic acid (110 mg, 0.67 mmol), and K2CO3 (141 mg, 1 mmol) in EtOH (1 mL) and H2O (1 mL) was added NDEAP-Al2O3-Pd(OAc)2 (256 mg, Pd loading: 0.1 mmol/g alumina, 0.026 mmol). After stirring for 5 min, the product was triturated with EtOAc several times. The combined organic layer was evaporated to dryness and the residue was purified by column chromatography (CH2Cl2-n-hexane, 3:10) to provide a biaryl product (121 mg, 100%).