Deoxygenative Tri- and Difluoromethylthiolation of Carboxylic Acids with Benzothiazolium Reagents
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.