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Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

Deoxygenative syntheses of fluorinated thioesters directly from carboxylic acids have been developed employing benzothiazolium reagents. The process using BT-SCF₃ represents an attractive approach toward these SCF₃-containing compounds that avoids the use of metal ^–SCF₃ salts or preactivated acyl electrophiles. Moreover, the in situ activation of BT-SCF₂H allows for an unprecedented nucleophilic difluoromethylthiolation reaction. DFT calculations support a mechanistic scenario involving a four-membered transition state where acyl substitution occurs without the formation of an unstable free ^–SCF₂H anion.

Publication metadata

Author(s): Tironi M, Maas LM, Garg A, Dix S, Götze JP, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2020

Volume: 22

Issue: 22

Pages: 8925-8930

Print publication date: 20/11/2020

Online publication date: 04/11/2020

Acceptance date: 29/10/2020

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.orglett.0c03328

DOI: 10.1021/acs.orglett.0c03328

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