Synthesis 2020; 52(05): 673-687
DOI: 10.1055/s-0039-1690038
short review
© Georg Thieme Verlag Stuttgart · New York

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Yan-Ping Meng
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
,
Shi-Meng Wang
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
b  School of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China
,
Wan-Yin Fang
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
b  School of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China
,
Zhi-Zhong Xie
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
,
Jing Leng
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
b  School of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China
,
Hamed Alsulami
c  Department of Mathematics, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
,
Hua-Li Qin
a  School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China   Email: qinhuali@whut.edu.cn
b  School of Materials Science and Engineering, Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province, 430070, P. R. of China
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (Grant No. 21772150), the Wuhan Applied Fundamental Research Plan of Wuhan Science and Technology Bureau (Grant No. 2017060201010216), the 111 Project (Grant No. B18038) and Wuhan University of Technology for the financial support.
Further Information

Publication History

Received: 23 October 2019

Accepted after revision: 18 November 2019

Publication Date:
09 December 2019 (online)


Abstract

The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.

1 Introduction

2 Chemical Transformations of ESF

3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides

4 Novel SuFEx Reagents Derived from ESF

5 Applications of ESF Derivatives in Medicinal Chemistry

6 Applications of ESF Derivatives in Materials Science

7 Conclusion

 
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