Synthesis of Ring-Fluorinated Thiophene Derivatives Based on Single C–F Bond Activation of CF3-Cyclopropanes: Sulfanylation and 5-endo-trig Cyclization | Zendy

Kohei Fuchibe | Zendy; Tatsuki Fushihara | Zendy; Junji Ichikawa | Zendy

Open Access

Synthesis of Ring-Fluorinated Thiophene Derivatives Based on Single C–F Bond Activation of CF₃-Cyclopropanes: Sulfanylation and 5-endo-trig Cyclization

Author(s) -

Kohei Fuchibe,

Tatsuki Fushihara,

Junji Ichikawa

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00385

Subject(s) - chemistry , regioselectivity , intramolecular force , ring (chemistry) , thiophene , solvent , medicinal chemistry , nucleophile , fluorine , nucleophilic substitution , sulfur , stereochemistry , organic chemistry , catalysis

The treatment of CF 3 -bearing cyclopropanes with E 2 AlCl generated stabilized difluorocarbocations, which underwent a nucleophilic addition of thiocarboxylic acids or thiols. The sulfur functionality was introduced at the position δ to the fluorine substituents in a regioselective manner (single activation of CF 3 -cyclopropanes). The formed 1,1-difluoro-1-alkenes underwent successive deesterification/5- endo - rig 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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research