Synlett 2014; 25(16): 2370-2374
DOI: 10.1055/s-0034-1378895
letter
© Georg Thieme Verlag Stuttgart · New York

A Novel Efficient Route for Acid-Catalyzed Synthesis of α,β-Alkynyl/Alkenyl Ketones

Xu Zhang*
School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China   Email: zhangxuedu@126.com
,
Xuefeng Xu
School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China   Email: zhangxuedu@126.com
,
Lintao Yu
School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China   Email: zhangxuedu@126.com
,
Zhiqiang Wang
School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China   Email: zhangxuedu@126.com
,
Qiang Zhao
School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China   Email: zhangxuedu@126.com
› Author Affiliations
Further Information

Publication History

Received: 06 May 2014

Accepted after revision: 11 July 2014

Publication Date:
13 August 2014 (online)


Abstract

Herein, we have developed a simple and efficient synthesis of α,β-alkynyl/alkenyl ketone derivatives by acid-catalyzed reactions of 2,6-dimethyl-N-(4-methylbenzylidene)aniline and alkynes. This methodology provides a novel pathway for the synthesis of α,β-alkynyl/alkenyl ketones via acid-catalyzed coupling reactions and subsequent silica gel catalyzed hydrolysis. Characterized by wide substrate scope, mild reaction conditions, and good to excellent yields this protocol may aid the further development of the C–C coupling reactions.

Supporting Information

 
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