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Synfacts 2010(4): 0397-0397  
DOI: 10.1055/s-0029-1219495
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Highly Substituted Furans from Alkynoates and 1,3-Dicarbonyls

Contributor(s): Victor Snieckus, Toni Rantanen
W. Liu, H. Jiang*, M. Zhang, C. Qi
South China University of Technology, Guangzhou, P. R. of China
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Reported is the construction of polysubstituted furans by copper-tin-catalyzed oxidative cyclization of 1,3-dicarbonyl compounds with alkynes. Extensive optimization of solvent, oxidant, and catalyst was carried out. Removing copper, tin, or the oxidant led to no product formation. A mechanism was proposed without evidence, in which copper(I) activates the dicarbonyl compound and SnCl2 activates the alkyne as a Lewis acid. The yields were generally good, but the substrate scope was inadequately studied.