Selective C(sp³)-S Bond Cleavage of Thioethers to Build Up Unsymmetrical Disulfides

Ke Yang*, Yanqi Luo, Qingyue Hu, Mengjie Song, Junxiang Liu, Zhengyi Li, Bijin Li* and Xiaoqiang Sun

*School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, China, Email: keyangcczu.edu.cn, bijinlicqu.edu.cn,

K. Yang, Y. Luo, Q. Hu, M. Song, J. Liu, Z. Li, B. Li, X. Sun, J. Org. Chem., 2023, 88, 13699-13711.

DOI: 10.1021/acs.joc.3c01355

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Abstract

While NBS achieves selective C(sp³)-S bond cleavage of furfuryl alkylthioethers at room temperature, NFSI mediates a selective methyl C(sp³)-S bond cleavage of aryl and alkyl methylthioethers at an elevated temperature. An in situ reaction with symmetrical disulfides provides unsymmetrical disulfides. This practical and operationally simple strategy offers excellent functional group tolerance.

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proposed mechanism

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Key Words

disulfides, NBS

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ID: J42-Y2023