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Chinese Journal of Organic Chemistry >

0 251014

DOI: https://doi.org/10.6023/cjoc202507003

ARTICLE

Intramolecular Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides for the Construction of Cycloalkano[c]furans

  • Guo Wentao ,
  • Meng Shuyu ,
  • Wang Quanrui
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  • aDepartment of Chemistry, Fudan University, Shanghai 200438

Received date: 2025-07-02

  Revised date: 2025-08-24

  Online published: 2025-10-15

Supported by

National Natural Science Foundation of China (No. 21971042).

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Abstract

An intramolecular tandem rearrangement for the synthesis of bicyclic furans is reported. The reaction was initiated by an intramolecular cross-coupling of the built-in alkynyl sulfoxide and alkynyl sulfide motifs in the presence of BF3·Et2O, followed by a [3,3]-sigmatropic sulfonium rearrangement and 5-exo-dig cyclization, affording cycloalkano[c]furans as final products in moderate yields with 100% atom economy. The synthetic utility of the resulting furans has been demonstrated through late-stage diversification by utilizing the alkylthio groups or the furan rings.

Key words： [3,3]-rearrangement; sulfonium ion; heterocyclization; cycloalkano[c]furan; intramolecular reaction

Cite this article

Guo Wentao , Meng Shuyu , Wang Quanrui . Intramolecular Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides for the Construction of Cycloalkano[c]furans[J]. Chinese Journal of Organic Chemistry, 0 : 251014 . DOI: 10.6023/cjoc202507003

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