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Synlett 2005(11): 1802-1804  
DOI: 10.1055/s-2005-871539
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© Georg Thieme Verlag Stuttgart · New York

Versatile Synthesis of 1,1-Diaryl-1-alkenes Using Vinylboronate Ester as a Platform

Keisuke Tonogakia, Kazuya Sogaa, Kenichiro Itami*b, Jun-ichi Yoshida*a
a Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
Fax: +81(75)3832727; e-Mail: yoshida@sbchem.kyoto-u.ac.jp;
b Research Center for Materials Science, Nagoya University, Nagoya 464-8602, Japan
e-Mail: itami@chem.nagoya-u.ac.jp;
Further Information

Publication History

Received 6 April 2005
Publication Date:
14 June 2005 (online)

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Abstract

A sequence of double Mizoroki-Heck reaction of vinylboronate pinacol ester with aryl halides followed by Suzuki-Miyaura coupling of thus-generated β,β-diarylvinylboronate esters with alkyl halides produces pharmaceutically important 1,1-diaryl-1-alkenes very efficiently. In the Pd-catalyzed Suzuki-Miyaura coupling step, the use of bulky electron-rich ligands such as P(t-Bu)2Me and PCy2(t-Bu) were found to be very effective.

Key words

palladium catalyst - Mizoroki-Heck reaction - Suzuki-Miyaura coupling - vinylboronate ester - alkyl halides

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