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Silver-Catalyzed Nucleophilic Deoxydifluoromethylthiolation of Activated Aliphatic Alcohols with BT−SCF₂H

Lookup NU author(s): Matteo Tironi, Dr Matt HopkinsonORCiD

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Abstract

Deoxygenative conversion of alcohols into difluoromethylthioethers is reported using 2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium triflate (BT-SCF₂H) as a source of ⁻SCF₂H anions. The presence of silver(I) triflate as a catalyst was found to be crucial for stabilizing the in situ-generated anion, while the concomitant formation of a reactive 2-(alkoxy)benzothiazolium electrophile likely ensures a fast onward substitution reaction, avoiding the build-up of ⁻SCF₂H. To the best of our knowledge, this process represents the first report of a direct nucleophilic substitution reaction with ⁻SCF₂H and delivers products containing the medicinally relevant difluoromethylthio motif in a single step from widely available alcohols.

Publication metadata

Author(s): Tironi M, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2022

Volume: 18

Print publication date: 13/05/2022

Online publication date: 08/04/2022

Acceptance date: 08/04/2022

Date deposited: 31/03/2022

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley-VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/ejoc.202101557

DOI: 10.1002/ejoc.202101557

ePrints DOI: 10.57711/03f4-kk71

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