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Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents

Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents

Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents
Image Credit: Reprinted with permission from Org. Lett. 2020, DOI: 10.1021/acs.orglett.0c03328. Copyright 2020 American Chemical Society.

M. Tironi,† L. M. Maas,† A. Garg, S. Dix, J. P. Götze, M. N. Hopkinson* – 2020

Deoxygenative syntheses of fluorinated thioesters directly from carboxylic acids have been developed employing benzothiazolium reagents. The process using BT-SCF3 represents an attractive approach towards these SCF3-containing compounds that avoids the use of metal −SCF3 salts or pre-activated 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.

Title
35. Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents
Author
M. Tironi,† L. M. Maas,† A. Garg, S. Dix, J. P. Götze, M. N. Hopkinson*
Publisher
Organic Letters
Date
2020
Identifier
DOI: 10.1021/acs.orglett.0c03328
Source(s)
Citation
Org. Lett. 2020, 22, 8925-8930.
Type
Text