Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Establishing the Trifluoromethylthio Radical Donating Abilities of Electrophilic SCF3-Transfer Reagents

Establishing the Trifluoromethylthio Radical Donating Abilities of Electrophilic SCF3-Transfer Reagents
Man Li, Biying Zhou, Xiao-Song Xue, Jin-Pei Cheng
The recent recognition of the novel application of a few traditional electrophilic trifluoromethylthiolating reagents as SCF3 radical sources offers a remarkable new opportunity for the development of radical trifluoromethylthiolation reactions. Herein, the first trifluoromethylthio radical donating ability (Tt•DA) scale of electrophilic SCF3-transfer reagents has been developed. This scale is based on Y-SCF3 bond dissociation energies, which were obtained by density functional calculations (M06-2X). Single electron transfer is revealed to exhibit a substantial Y-SCF3 bond-weakening effect, thus significantly facilitating the SCF3 radical (•SCF3) release. The results may aid in future novel radical SCF3-transfer reagent design and new reaction development.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01771

DOI: 10.1021/acs.joc.7b01771

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