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Access to N-Difluoromethyl Amides, (Thio)Carbamates, Ureas, and Formamides.

ABSTRACT: The first efficient access to N-difluoromethyl amides, carbamates, thiocarbamates, ureas, formamides, and their derivatives is reported herein. The synthetic strategy relies on the initial synthesis and straightforward derivatization of N-CF₂H carbamoyl fluorides, which were prepared through a desulfurization-fluorination of thioformamides (─NH─C(H)═S) coupled with carbonylation. The newly made N-CF₂H carbonyl compounds proved to be highly robust and compatible with numerous chemical transformations and downstream derivatizations, underscoring the potential of this novel motif as a building block in complex functional molecules.

SUBMITTER: Zivkovic FG

PROVIDER: S-EPMC10913043 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Access to N-Difluoromethyl Amides, (Thio)Carbamates, Ureas, and Formamides.

Zivkovic Filip G FG Wycich Gina G Liu Linhao L Schoenebeck Franziska F

Journal of the American Chemical Society 20240105 2

The first efficient access to N-difluoromethyl amides, carbamates, thiocarbamates, ureas, formamides, and their derivatives is reported herein. The synthetic strategy relies on the initial synthesis and straightforward derivatization of N-CF2H carbamoyl fluorides, which were prepared through a desulfurization-fluorination of thioformamides (─NH─C(H)═S) coupled with carbonylation. The newly made N-CF2H carbonyl compounds proved to be highly robust and co ...[more]

PMID: 38180777

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