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Synthesis 2008(19): 3047-3052  
DOI: 10.1055/s-2008-1067253
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient One-Pot Synthesis of Bis[(E)-4-halostyryl]arene Derivatives

Wiesław Prukała, Mariusz Majchrzak, Krystian Posała, Bogdan Marciniec*
Department of Organometallic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8291508; e-Mail: marcinb@amu.edu.pl;
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Publication History

Received 17 March 2008
Publication Date:
04 September 2008 (online)

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Abstract

A new convenient synthetic protocol for the one-pot stereoselective synthesis of bis[(E)-4-bromo(or chloro)styryl]arene derivatives via the sequential reaction of silylative-coupling of 4-halostyrenes with vinylsilanes followed by palladium-catalyzed cross-coupling 4-halostyrylsilanes with diiodoarenes, is described. The reaction leads to symmetrical bis[(E)-4-halostyryl]arene derivatives obtained in a stereocontrolled manner with high efficiency.

Key words

vinylsilanes - transition metals catalysis - silylative cross-coupling

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