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

doi:10.6023/cjoc202507003

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炔基亚砜的分子内交叉偶联/[3,3]-硫鎓离子重排策略构建环烷并[c]呋喃

郭闻涛, 孟书玉, 王全瑞^*

复旦大学化学系上海 200438

收稿日期:2025-07-02 修回日期:2025-08-24
基金资助:
国家自然科学基金(No. 21971042)资助项目.

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

Guo Wentao^a, Meng Shuyu^a, Wang Quanrui^a,*

^aDepartment of Chemistry, Fudan University, Shanghai 200438

Received:2025-07-02 Revised:2025-08-24
Contact: *E-mail: E-mail: qrwang@fudan.edu.cn
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

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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, doi: 10.6023/cjoc202507003.

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炔基亚砜的分子内交叉偶联/[3,3]-硫鎓离子重排策略构建环烷并[c]呋喃

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

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