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Exploiting a “Beast” in Carbenoid Chemistry: Development of a Straightforward Direct Nucleophilic Fluoromethylation Strategy

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posted on 11.09.2017 by Giovanna Parisi, Marco Colella, Serena Monticelli, Giuseppe Romanazzi, Wolfgang Holzer, Thierry Langer, Leonardo Degennaro, Vittorio Pace, Renzo Luisi
The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a “fleeting” lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

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