Synthesis of Benzo-Thioethers Based on Intramolecular Selective C-S Cleavage of Arylthianthreniums

doi:10.7503/cjcu20240538

Chem. J. Chinese Universities

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Synthesis of Benzo-Thioethers Based on Intramolecular Selective C-S Cleavage of Arylthianthreniums

NAN Jiang，XU Kailun，YAN Qiang

Shaanxi University of Science and Technology

Received:2024-12-11 Revised:2025-02-06 Online:2025-02-14 Published:2025-02-14
Contact: Jiang Nan E-mail:nanjiang@sust.edu.cn
Supported by:
Supported by the National Natural Science Foundation(No.22171171)，Innovative Talent Promotion Plan-Young Science and Technology Star Project (No.2022KJXX-15), and Shaanxi Provincial Association for Science and Technology (No.20200605)

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Abstract

Abstract: Here reported is an intramolecular nucleophilic substitution reaction of aryl-thianthrenium salts, which conducts the selective cleavage of C-O and C-S chemical bonds. This finding represents a novel chemical property and conversion with aryl-thianthreniums, rapidly assembling the highly conjugated tribenzo-thioester compounds. Of note, this developed methodology is charactered by excellent functional group tolerance, good productivities, and metal-free trait. This conversion delivers 23 examples of structurally innovative nine-membered thioethers, which puts forward an alternative synthesizing route for the widely used crown ethers.

Key words: Arylthianthreniums; C—S Bond cleavage, Benzo-thioesters

CLC Number:

O626

TrendMD:

NAN Jiang, XU Kailun, YAN Qiang. Synthesis of Benzo-Thioethers Based on Intramolecular Selective C-S Cleavage of Arylthianthreniums[J]. Chem. J. Chinese Universities, doi: 10.7503/cjcu20240538.

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Synthesis of Benzo-Thioethers Based on Intramolecular Selective C-S Cleavage of Arylthianthreniums

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