Synlett 2008(10): 1529-1531  
DOI: 10.1055/s-2008-1078412
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct One-Pot Synthesis of 2,3-Diarylbuta-1,3-diene via Self-Coupling of Acetophenones

Jian Li, Shaoyu Li, Xueshun Jia*
Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China
Fax: +86(21)66132797; e-Mail: xsjia@mail.shu.edu.cn;
Further Information

Publication History

Received 25 February 2008
Publication Date:
16 May 2008 (online)

Abstract

A mild and straightforward route to 2,3-diarylbuta-1,3-diene is described here. By treatment with SmI2-Ac2O, acetophenone and its analogues underwent self-coupling reactions and subsequent elimination to give a series of 2,3-diarylbuta-1,3-dienes in moderate to good yields.

    References and Notes

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10

General Procedure for the Synthesis of 2,3-Diarylbuta-1,3-dienes (Method A): To the stirred acetophenone or its analogues 1 (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, Ac2O (1.2 mmol) was added to the yellow mixture rapidly. The reaction mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding pure buta-1,3-diene 2.
General Procedure for the Synthesis of 2,3-Bis(4-bromophenyl)buta-1,3-diene and 2,3-Bis(4-chloro-phenyl)buta-1,3-diene (Method B): To the stirred 4-chloro- or 4-bromo-substituted acetophenone (1 mmol) in an oven-dried glassware under a nitrogen atmosphere, samarium diiodide (1 mmol) in THF (15 mL) was added dropwise. Generally the reaction finished within 15 min. After the deep blue color faded, THF was removed under reduced pressure, then MeCN (3 mL) and Ac2O (3.0 mmol) were added to the yellow mixture successively, and the resulting mixture was stirred under reflux until reaction completion. After the usual workup, the crude product was purified by silica gel column chromatography using EtOAc-PE (1:20) as eluent to afford the corresponding diene.