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Synthesis 2019; 51(18): 3410-3418
DOI: 10.1055/s-0037-1611567
DOI: 10.1055/s-0037-1611567
paper
Palladium(II) Acetate Mediated Dimerization/Cycloisomerization of 2-Sulfonyl-4-alkynones: Synthesis of trans-1,2-Difurylethylenes
The authors would like to thank the Ministry of Science and Technology of the People’s Republic of China for financial support (MOST 106-2628-M-037-001-MY3).Further Information
Publication History
Received: 08 April 2019
Accepted after revision: 06 May 2019
Publication Date:
23 May 2019 (online)
Abstract
This paper describes a one-pot, atom-economic, easy-operation, open-atmosphere method for the synthesis of trans-1,2-difurylethylenes by the straightforward Pd(OAc)2-mediated dimerization/cycloisomerization of 2-sulfonyl-4-alkynones in the presence of Na2CO3 and PPh3 under refluxing EtOH conditions, and proposes and discusses a plausible mechanism. This protocol provides a highly effective annulation via two carbon–oxygen (C–O) single-bond and one carbon–carbon (C=C) double-bond formations.
Key words
palladium(II) acetate - dimerization/cycloisomerization - 4-alkynones - 1,2-difurylethylenes - one-pot atom-economic methodSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611567.
- Supporting Information
- CIF File
-
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For reviews on 1,2-diarylethylenes, see:
For recent syntheses of 1,2-diarylethylenes, see:
For selected examples of the synthesis of 1,2-dipyridylethylenes, see:
For selected examples of the synthesis of 1,2-dithienylethylenes, see:
For syntheses of 1,2-difurylethylenes, see:
For examples of the synthesis of vinylfurans, see:
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For examples of the palladium-mediated synthesis of substituted furans via the annulation of alkynes, see: