Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 20, Pages 5606-5610Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00962e
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Funding
- NSFC [22101044]
- Department of Science and Technology of Jilin Province [20210508045RQ, 20200801065GH]
- Fundamental Research Funds for the Central Universities [2412020ZD003]
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A metal-free cycloaddition reaction of fluoroalkyl N-sulfonylhydrazones with arene-diazonium salts to form fluoroalkylated tetrazole products was reported. This procedure provides a general and safe method for accessing mono-, di-, and perfluoroalkyl tetrazoles with excellent yields and tolerance of diverse functional groups.
Herein we reported a metal-free cycloaddition reaction of fluoroalkyl N-sulfonylhydrazones with arene-diazonium salts to form the corresponding fluoroalkylated tetrazole products. This transformation represents the first general and operationally safe procedure to access mono-, di- and perfluoroalkyl tetrazole products. A total of 77 previously inaccessible fluoroalkyl tetrazoles were reported in good-to-excellent yields, with excellent tolerance of diverse functional groups. Moreover, monofluoroalkyl N-triftosylhydrazone (MFHZ-Tfs) was synthesised for the first time, and was applied as a mono-fluoromethyldiazo reagent.
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