Synthesis 2019; 51(20): 3825-3833
DOI: 10.1055/s-0039-1690003
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of 2-Acylbutadienes from β,γ-Unsaturated Ketones

Dmitrii A. Shabalin
,
Elena V. Ivanova
,
Igor A. Ushakov
,
Elena Yu. Schmidt
,
Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author Affiliations
The reported study was funded by RFBR according to the research project No. 18-33-00100.
Further Information

Publication History

Received: 28 May 2019

Accepted after revision: 26 June 2019

Publication Date:
15 July 2019 (online)


Abstract

2-Acylbuta-1,3-dienes have been synthesized regioselectively from aromatic and heteroaromatic β,γ-unsaturated ketones (readily accessible via base-catalyzed addition of ketones to acetylenes) and aldehydes. The reaction smoothly proceeds with piperidine (10 mol%)/acetic acid (10 mol%) catalytic pair in boiling toluene to provide synthetically attractive polyconjugated electron-deficient dienes in up to 94% yield.

Supporting Information

 
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