An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

doi:10.1007/s40242-018-7305-0

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (2): 191-196.doi: 10.1007/s40242-018-7305-0

An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

JING Li¹, YU Xinling¹, GUAN Mei², WU Xiaohua¹, WANG Qiantao¹, WU Yong¹

1. Key Laboratory of Drug-targeting of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China;
2. West China Hospital, Sichuan University, Chengdu 610041, P. R. China

收稿日期:2017-09-13 修回日期:2017-11-17 出版日期:2018-04-01 发布日期:2017-12-18
通讯作者: WANG Qiantao,E-mail:qwang@scu.edu.cn;WU Yong,E-mail:wyong@scu.edu.cn E-mail:qwang@scu.edu.cn;wyong@scu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).

An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

JING Li¹, YU Xinling¹, GUAN Mei², WU Xiaohua¹, WANG Qiantao¹, WU Yong¹

1. Key Laboratory of Drug-targeting of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China;
2. West China Hospital, Sichuan University, Chengdu 610041, P. R. China

Received:2017-09-13 Revised:2017-11-17 Online:2018-04-01 Published:2017-12-18
Contact: WANG Qiantao,E-mail:qwang@scu.edu.cn;WU Yong,E-mail:wyong@scu.edu.cn E-mail:qwang@scu.edu.cn;wyong@scu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).

摘要/Abstract

摘要： A new and convenient procedure was developed for the preparation of sulfonamides and sulfonic esters using N-fluorobenzenesulfonimide(NFSI) as a novel phenylsulfonyl group transfer reagent. In this protocol, a broad range of functional groups were tolerated to give the corresponding sulfonamides or sulfonic esters in moderate to excellent yields. The synthetic strategy for sulfonamides formation proceeded efficiently even under base-, metal-and additive-free conditions with the advantages of operational simplicity, mild reaction conditions as well as short reaction time.

关键词: N-Fluorobenzenesulfonimide, Sulfonylation, Sulfonamide, Sulfonic ester

Abstract: A new and convenient procedure was developed for the preparation of sulfonamides and sulfonic esters using N-fluorobenzenesulfonimide(NFSI) as a novel phenylsulfonyl group transfer reagent. In this protocol, a broad range of functional groups were tolerated to give the corresponding sulfonamides or sulfonic esters in moderate to excellent yields. The synthetic strategy for sulfonamides formation proceeded efficiently even under base-, metal-and additive-free conditions with the advantages of operational simplicity, mild reaction conditions as well as short reaction time.

Key words: N-Fluorobenzenesulfonimide, Sulfonylation, Sulfonamide, Sulfonic ester

JING Li, YU Xinling, GUAN Mei, WU Xiaohua, WANG Qiantao, WU Yong. An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions[J]. 高等学校化学研究, 2018, 34(2): 191-196.

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An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

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