Synthesis and 18F Labeling of Alkenyl Sulfonyl Fluorides via an Unconventional Elimination Pathway

Wei Zhang; Xiaoyun Deng; Feng-Xu Zhang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang

doi:10.1021/acs.orglett.2c02091

Synthesis and ¹⁸F Labeling of Alkenyl Sulfonyl Fluorides via an Unconventional Elimination Pathway

Org Lett. 2022 Jul 15;24(27):4992-4997. doi: 10.1021/acs.orglett.2c02091. Epub 2022 Jun 30.

Authors

Wei Zhang¹, Xiaoyun Deng^{2

3}, Feng-Xu Zhang¹, Jin-Hong Lin^{1

4}, Ji-Chang Xiao¹, Steven H Liang²

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032 Shanghai, China.
² Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital, and Department of Radiology, Harvard Medical School, 55 Fruit Street, White 427, Boston, Massachusetts 02114, United States.
³ Department of Nuclear Medicine, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, 1095 Jiefang Avenue, 430030 Wuhan, China.
⁴ Department of Chemistry, Innovative Drug Research Center, Shanghai University, 200444 Shanghai, China.

PMID: 35771975
DOI: 10.1021/acs.orglett.2c02091

Abstract

A successful Cu-catalyzed addition of both Cl and SO₂OCF₂H groups into alkenes allows us to discover the unusual reactivity of the SO₂OCF₂H group. As opposed to common sulfonic esters (RSO₂-O-R'), in which the R' group is highly electrophilic, the SO₂ moiety demonstrates higher electrophilicity in RSO₂-OCF₂H. The unexpected reactivity is further developed not only as a synthetic tool for well-functionalized alkenyl sulfonyl fluorides but also for the first ¹⁸F labeling of alkenyl sulfonyl fluorides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes
Esters
Fluorides*
Sulfinic Acids*

Substances

Alkenes
Esters
Sulfinic Acids
sulfuryl fluoride
Fluorides