Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced Hunsdiecker-Type Reaction

Chunxiang Kuang; Qing Yang; Hisanori Senboku; Masao Tokuda

doi:10.1055/s-2005-865283

PAPER

Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced Hunsdiecker-Type Reaction

Chunxiang Kuang*^a, Qing Yang^b, Hisanori Senboku^c, Masao Tokuda^c
^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

Abstract

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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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References

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