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| PAPER | Synthesis 2005: 1319-1325
DOI: 10.1055/s-2005-865283 |
© Georg Thieme Verlag Stuttgart · New York
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Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced Hunsdiecker-Type Reaction
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| Chunxiang Kuang*a, Qing Yangb, Hisanori Senbokuc, Masao Tokudac |
a Department of Materials Chemistry, Graduate School of Engineering, Osaka University, Suita 565-0871, Japan
Fax: +81(6)68505785; e-Mail: kuang@ch.wani.osaka-u.ac.jp;
b Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, 060-8589, Japan
c Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
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Received
2 December 2004 |
Abstract
(E)-β-Arylvinyl bromides were readily prepared in a short reaction time (1-2 min) by microwave irradiation of the corresponding 3-arylpropenoic acids in the presence of N-bromosuccinimide and a catalytic amount of lithium acetate. Furthermore, two facile strategies for the efficient synthesis of (E)-β-bromo-4-arylethynylstyrene and (E)-β-bromo-4-arylstyrene have been developed by respectively combining Sonogashira and Suzuki coupling reaction with Hunsdiecker-type reaction. Formation of cis-α-bromo-β-lactone by microwave irradiation of cis-cinnamic acid with NBS provides a useful support for the mechanistic study of the present halodecarboxylation reaction. Key words
(E)-β-arylvinyl bromides - α,β-unsaturated carboxylic acids - stereoselective synthesis - microwave irradiation - Hunsdiecker-type reaction
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