Journal
ORGANIC LETTERS
Volume 24, Issue 27, Pages 4992-4997Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02091
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Funding
- National Key Research and Development Program of China [2021YFF0701700]
- National Natural Science Foundation [21971252, 21991122]
- Key Research Program of Frontier Sciences
- Chinese Academy of Sciences (CAS) [QYZDJSSWSLH049]
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This study discovered the unusual reactivity of the SO2OCF2H group and successfully developed a synthetic tool for well-functionalized alkenyl sulfonyl fluorides, as well as achieving the first 18F labeling of alkenyl sulfonyl fluorides.
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 & PRIME; 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.
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