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Synlett 2005(6): 1039-1041  
DOI: 10.1055/s-2005-863750
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct and Highly Efficient Synthesis of (Z)-Allyl Iodides from Baylis-Hillman Adducts Promoted by TMSCl/NaI System

Jian Lia, Xiaoxia Wangb, Yongmin Zhang*a,c
a Department of Chemistry, Zhejiang University, Xi-xi Campus, Hangzhou, 310028, P. R. China
Fax: +86(571)88807077; e-Mail: yminzhang@mail.hz.zj.cn;
b College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, Zhejiang, 321004, P. R. China
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China
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Publication History

Received 12 January 2005
Publication Date:
23 March 2005 (online)

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Abstract

Direct and efficient transformation of Baylis-Hillman adducts into corresponding (Z)-allyl iodides has been achieved by treatment with TMSCl/NaI in THF at room temperature. The readily available reagents, mild conditions together with its generality make this procedure quite attractive.

Key words

Baylis-Hillman adduct - (Z)-allyl iodide - TMSCl/NaI