Citation: Jing Fang, Ting Li, Xiang Ma, Jiuchang Sun, Lei Cai, Qi Chen, Zhiwen Liao, Lingkui Meng, Jing Zeng, Qian Wan. Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions[J]. Chinese Chemical Letters, ;2022, 33(1): 288-292. doi: 10.1016/j.cclet.2021.06.069 shu

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, Wuhan 430030, China

wanqian@hust.edu.cn

Received Date: 15 April 2021
Revised Date: 22 June 2021
Accepted Date: 25 June 2021
Available Online: 2 July 2021

Figures(3)

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
- Sulfonium ylide,
- Alkylation,
- Arylation,
- Non-ylidic C-S bond cleavage
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