Issue 4, 2019
From the journal:

Organic Chemistry Frontiers

Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide†

Qiongzhen Lin,‡ab   Yongan Liu,‡b   Zhiwei Xiao,b   Liping Zheng,c   Xiumiao Zhou,c   Yong Guo, ORCID logo b   Qing-Yun Chen,b   Changge Zheng*a  and  Chao Liu ORCID logo *b  

* Corresponding authors

a School of Chemical Engineering, Xinjiang Agricultural University, Urumqi, Xinjiang Uygur Autonomous Region 830052, China
E-mail: cgzheng@jiangnan.edu.cn

b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: chaoliu@sioc.ac.cn

c School of Chemical Engineering and Food Science, Zhengzhou Institute of Technology, 18 Yingcai Street, Zhengzhou 450044, China

Abstract

An intermolecular oxidative radical fluoroalkylfluorosulfonylation reaction of unactivated alkenes with convenient and commercially available (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide (NFSI) is described. This transformation efficiently affords various fluoroalkyl-containing alkyl sulfonyl fluorides with good functional group tolerance under mild conditions. Silver fluoroalkyl complexes as the fluoroalkyl radical source generated from (fluoroalkyl)trimethylsilane and silver fluoride may be the key intermediate.

Graphical abstract: Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

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Article information

DOI
https://doi.org/10.1039/C8QO01192C
Article type
Research Article
Submitted
03 Nov 2018
Accepted
16 Dec 2018
First published
19 Dec 2018

Org. Chem. Front., 2019,6, 447-450

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Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

Q. Lin, Y. Liu, Z. Xiao, L. Zheng, X. Zhou, Y. Guo, Q. Chen, C. Zheng and C. Liu, Org. Chem. Front., 2019, 6, 447 DOI: 10.1039/C8QO01192C

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