Synlett 2014; 25(16): 2341-2344
DOI: 10.1055/s-0034-1379213
letter
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Synthesis of 2,5-Disubstituted Furans from Enyne Acetates Catalyzed by Lewis Acid and Palladium

Zheng-Wang Chen*
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
,
Miao-Ting Luo
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
,
Yue-Lu Wen
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
,
Min Ye
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
,
Zhong-Gao Zhou
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
,
Liang-Xian Liu*
School of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi, 341000, P. R. of China   Fax: +86(797)8393670   Email: chenzwang@gnnu.cn
› Author Affiliations
Further Information

Publication History

Received: 02 June 2014

Accepted after revision: 11 July 2014

Publication Date:
08 September 2014 (online)


Abstract

A highly efficient synthesis of a wide range of 2,5-disubstituted furans from enyne acetates is described. The reactions are conducted by using Lewis acid and palladium catalyst and provide symmetrical and unsymmetrical products in good to excellent yields, with broad substrate scope, including a variety of aromatic and aliphatic substituents in the 2- and 5-position of the furan ring.

Supporting Information

 
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  • 18 Preparation of 2,5-Disubstituted Furans from Enyne Acetates; Typical Procedure: To a mixture of (Z)-1,4-diphenylbut-1-en-3-yn-1-yl acetate (1a; 0.25 mmol) and MeNO2 (1.0 mL), Pd(OAc)2 (5 mol%), BF3·OEt2 (30 mol%), and H2O (1 equiv) were added. The mixture was stirred at 80 °C for 10 h, then H2O (10 mL) was added and the solution was extracted with EtOAc (3 × 8 mL). The combined extract was dried with anhydrous MgSO4, the solvent was removed, and the residue was separated by column chromatography (petroleum ether–EtOAc, 30:1) to give the desired product 2a.