Transition-Metal-Free Reaction of α-Bromonitriles with Thiosulfonates: Synthesis of α-Sulfonyl-α-(aryl/alkylthio)nitriles

doi:10.6023/cjoc202605022

Chinese Journal of Organic Chemistry

ARTICLE

无过渡金属条件下α-溴代腈与硫代磺酸酯的反应研究：合成α-砜基-α-芳/烷硫基腈

张宇杭, 杨益民, 姜佳佳, 姚秋丽^*, 黄洋^*

遵义医科大学药学院贵州省化学药物创制全省重点实验室贵州遵义 563003

收稿日期:2026-05-20 修回日期:2026-07-20
基金资助:
遵义医科大学(No. F-1119)、贵州省教育厅自然科学研究项目([2024]334)资助

Transition-Metal-Free Reaction of α-Bromonitriles with Thiosulfonates: Synthesis of α-Sulfonyl-α-(aryl/alkylthio)nitriles

Zhang Yuhang, Yang Yimin, Jiang Jiajia, Yao Qiuli^*, Huang Yang^*

Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563003

Received:2026-05-20 Revised:2026-07-20
Contact: *E-mail: ylovt@126.com; yanghuang@zmu.edu.cn
Supported by:
Zunyi Medical University (No. F-1119), Natural Science Research Project of Guizhou Provincial Department of Education (No. [2024]334).

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Abstract

We report a transition-metal-free difunctionalization reaction of thiosulfonates with α-bromonitriles, enabling the efficient synthesis of α-sulfonyl-(aryl/alkylthio)nitrile derivatives. In a single step, this protocol simultaneously constructs two distinct carbon-sulfur bonds at the α-position of the cyano group, thereby providing a new approach to all-carbon quaternary centers bearing cyano, sulfonyl, and aryl/alkylthio groups. The method exhibits broad substrate scope and excellent functional-group tolerance: substrates bearing either electron-withdrawing or electron-donating substituents afford the corresponding α-sulfonyl-α-(aryl/alkylthio)nitrile derivatives in moderate to excellent yields. Notably, this protocol features mild reaction conditions, operational simplicity, and high atom economy.

Key words: α-bromonitriles, thiosulfonates, difunctionalization, α-sulfonyl-α-(aryl/alkylthio)nitrile

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Zhang Yuhang, Yang Yimin, Jiang Jiajia, Yao Qiuli, Huang Yang. Transition-Metal-Free Reaction of α-Bromonitriles with Thiosulfonates: Synthesis of α-Sulfonyl-α-(aryl/alkylthio)nitriles[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202605022.

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无过渡金属条件下α-溴代腈与硫代磺酸酯的反应研究：合成α-砜基-α-芳/烷硫基腈

Transition-Metal-Free Reaction of α-Bromonitriles with Thiosulfonates: Synthesis of α-Sulfonyl-α-(aryl/alkylthio)nitriles

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