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Synfacts 2009(7): 0721-0721  
DOI: 10.1055/s-0029-1217385
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Furans via Copper-Catalyzed Domino Reactions

Contributor(s): Victor Snieckus, Jignesh P. Patel
H. Cao, H. Jiang*, W. Yao, X. Liu
South China University of Technology, Guangzhou, P. R. of China
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

Reported here is a copper(I)-catalyzed synthesis of highly substituted furan derivatives from 1,5-enynes (generated in situ from diethyl but-2-ynedioate and alkynols). A plausible mechanism is described here that consists of a 6-endo-dig cyclization of B followed by the rearrangement of species C to generate the β-allenic ketone D. The species D was converted into carbene complex E which underwent sequential dehydrogenation oxidation followed by carbene oxidation (under atmospheric pressure) to the furan.