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Deuterium-labeled compounds are playing key roles in many scientific fields such as pharmaceutical science and mechanistic studies of organic reactions.1­3 One of the most facile and straightforward methods to introduce a deuterium atom selectively is reductive halogen-deuterium exchange reactions. Several conditions, such as using a radical mediator (e.g. tin hydride4­7 and samarium diiodide8) or light irradiation,9 have been reported. Meanwhile, we have studied electro-organic transformations,10­13 and recently reported electro-reductive intramolecular cyclization of haloarenes bearing an alkene moiety in acetonitrile.14 During the course of the mechanistic study on the reactions, we found that the cyclized radical intermediate would be protonated by acetonitrile, and the reaction in CD3CN gave deuterated product selectively. These results prompted us to study an electro-reductive halogen-deuterium exchange reaction under metal-free and mild conditions. Screening of the reaction conditions revealed that 9-fluorenone was an efficient mediator for the reaction, and we unexpectedly found that dehalomethylation also proceeded under similar conditions. We herein report the first electro-reductive halogen-deuterium exchange reaction and methylation reaction.

Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile