Abstract
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.
Original language | English |
---|---|
Pages (from-to) | 13648–13651 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 139 |
Issue number | 39 |
DOIs | |
Publication status | Published - 4 Oct 2017 |
Austrian Fields of Science 2012
- 104001 General chemistry
Keywords
- ALLYLIC ALCOHOLS
- CARBANIONS
- ENANTIOSELECTIVE SYNTHESIS
- FLUORINE
- FLUOROBIS(PHENYLSULFONYL)METHANE
- FUNCTIONAL-GROUPS
- LATE-STAGE
- MEDICINAL CHEMISTRY
- MONOFLUOROMETHYLATION
- PALLADIUM