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Synlett 2009(19): 3151-3154  
DOI: 10.1055/s-0029-1218283
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Cross-Coupling of Arylboronic Acids Using Vinyl Acetate as the Electrophilic Partner

Hang Wai Lee, Fuk Yee Kwong*
Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, P. R. of China
Fax: +85223649932; e-Mail: bcfyk@inet.polyu.edu.hk;
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Publikationsverlauf

Received 27 July 2009
Publikationsdatum:
23. Oktober 2009 (online)

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Abstract

The first Suzuki-type cross-coupling between arylboronic acids and vinyl acetate is disclosed. The acetoxy moiety as the leaving group is realized in the coupling process. Rhodium complexes were found to be highly effective for promoting this transformation. In contrast, the present well-known nickel and palladium complexes were inferior for this catalysis when vinyl acetate was used as the electrophilic partner.

Key words

cross-coupling - catalysis - rhodium - vinyl acetate

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15

We tried to lower the loading of vinyl acetate to 2 equiv (with respected to arylboronic acid). However, the product yield dropped significantly.