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Synlett 2014; 25(16): 2341-2344
DOI: 10.1055/s-0034-1379213
DOI: 10.1055/s-0034-1379213
letter
A Highly Efficient Synthesis of 2,5-Disubstituted Furans from Enyne Acetates Catalyzed by Lewis Acid and Palladium
Further Information
Publication History
Received: 02 June 2014
Accepted after revision: 11 July 2014
Publication Date:
08 September 2014 (online)
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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
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- 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.
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