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A Systematic Assessment of Trifluoromethyl Radical Donor Abilities of Electrophilic Trifluoromethylating Reagents
Author(s) -
Li Man,
Wang Ya,
Xue XiaoSong,
Cheng JinPei
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600539
Subject(s) - trifluoromethylation , chemistry , electrophile , homolysis , reagent , trifluoromethyl , combinatorial chemistry , radical ion , bond dissociation energy , bond cleavage , dissociation (chemistry) , organic chemistry , medicinal chemistry , computational chemistry , photochemistry , radical , catalysis , ion , alkyl
Identifying the ability of traditional electrophilic trifluoromethylating reagents as CF 3 · radical sources offers a great opportunity for developing new radical trifluoromethylation reactions. Herein, we report the first extensive assessment of the propensity of these reagents to donate a CF 3 · radical by computing X−CF 3 bond homolytic dissociation enthalpies. Single electron reduction has a substantial effect on activating the X−CF 3 bond, thereby significantly facilitating a CF 3 radical release. The quantitative information provided here could be valuable for mechanistic understanding and the rational design of new radical trifluoromethylation reactions.

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