A Systematic Assessment of Trifluoromethyl Radical Donor Abilities of Electrophilic Trifluoromethylating Reagents

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• 作者：Man Li ; Ya Wang ; Prof. Dr. Xiao-Song Xue and Prof. Dr. Jin-Pei Cheng
• 刊名：Asian Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：6
• 期：2
• 页码：235-240
• 全文大小：1963K
• ISSN：2193-5815

文摘

Identifying the ability of traditional electrophilic trifluoromethylating reagents as CF₃^· 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 CF₃^· radical by computing X−CF₃ bond homolytic dissociation enthalpies. Single electron reduction has a substantial effect on activating the X−CF₃ bond, thereby significantly facilitating a CF₃ radical release. The quantitative information provided here could be valuable for mechanistic understanding and the rational design of new radical trifluoromethylation reactions.