Palladium(II) Acetate Mediated Dimerization/Cycloisomerization of 2-Sulfonyl-4-alkynones: Synthesis of trans-1,2-Difurylethylenes

Meng-Yang Chang; Kai-Xiang Lai

doi:10.1055/s-0037-1611567

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3410-3418
DOI: 10.1055/s-0037-1611567

paper

Palladium(II) Acetate Mediated Dimerization/Cycloisomerization of 2-Sulfonyl-4-alkynones: Synthesis of trans-1,2-Difurylethylenes

Meng-Yang Chang *

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan Email: mychang@kmu.edu.tw

,

Kai-Xiang Lai

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan

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Abstract

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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 method

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References

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