Journal
ORGANIC LETTERS
Volume 22, Issue 6, Pages 2201-2205Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00385
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Funding
- JSPS KAKENHI [JP18H04234, JP19H02707]
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The treatment of CF3-bearing cyclopropanes with Et2AlCl generated stabilized difluorocarbocations, which underwent a nucleophilic addition of thiocarboxylic acids or thiols. The sulfur functionality was introduced at the position delta to the fluorine substituents in a regioselective manner (single activation of CF3-cyclopropanes). The formed 1,1-difluoro-1-alkenes underwent successive deesterification/5-endo-trig cyclization. Intramolecular vinylic substitution proceeded in an aprotic solvent, whereas intramolecular addition proceeded in a protic solvent to afford pharmaceutically and agrochemically promising 2-fluoro-4,5-dihydrothiophene and 2,2-difluorotetrahydrothiophene scaffolds, respectively.
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