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Synthesis 2008(16): 2650-2658  
DOI: 10.1055/s-2008-1067195
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Indenes and cis-Stilbenoid Hydrocarbons via Palladium-Catalyzed Domino Reactions of Hindered Grignard Reagents with (E)-1,2-Dibromoethenes

Cheng-Guo Dong, Tao-Ping Liu, Qiao-Sheng Hu*
Department of Chemistry, College of Staten Island and the Graduate Center, City University of New York, Staten Island, NY 10314, USA
Fax: +1(718)9823910; e-Mail: qiaohu@mail.csi.cuny.edu;
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Publication History

Received 21 April 2008
Publication Date:
24 July 2008 (online)

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Abstract

Palladium-catalyzed domino reactions of (E)-1,2-dibromoethenes with hindered Grignard reagents based on carbopalladation, palladium-catalyzed cross-coupling, and C-H activation are described. These domino reactions could be influenced by the ligand, reaction temperature, nucleophilicity of Grignard reagents, and steric hindrance of the substrates. Our study provides an efficient access to some useful polysubstituted indenes and cis-substituted stilbenes, and may be useful for the development of other cross-coupling and C-H activation-based tandem/domino reactions.

Key words

palladium - Grignard reactions - domino reactions - cyclization­ - cross-coupling

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