Metal-Catalyzed Fluoroacetyl Carbene Transfer from Sulfonium Salts DOI Creative Commons

Arturs Sperga,

Artis Kinēns, Janis Veliks

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

The synthesis of organofluorine compounds is pivotal in developing innovative pharmaceuticals, materials, and agrochemicals. Fluorinated carbene transfer offers a promising strategy for forming new carbon-carbon carbon-heteroatom bonds, facilitating one-carbon editing by simultaneously introducing fluorine into target structures. In this study, we introduce novel fluoroacetyl sulfonium reagent, (2-ethoxy-1-fluoro-2-oxoethyl)(phenyl)(2,3,4,5-tetramethylphenyl)sulfonium tetrafluoroborate (1), serving as an effective alternative to the currently unknown 2-diazo-2-fluoroacetate ethyl transfer. This reagent applied Doyle-Kirmse cyclopropanation reactions operating under mild conditions with use earth-abundant metal catalysts. approach enables efficient valuable monofluorinated products.

Language: Английский

Metal-Catalyzed Fluoroacetyl Carbene Transfer from Sulfonium Salts DOI Creative Commons

Arturs Sperga,

Artis Kinēns, Janis Veliks

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

The synthesis of organofluorine compounds is pivotal in developing innovative pharmaceuticals, materials, and agrochemicals. Fluorinated carbene transfer offers a promising strategy for forming new carbon-carbon carbon-heteroatom bonds, facilitating one-carbon editing by simultaneously introducing fluorine into target structures. In this study, we introduce novel fluoroacetyl sulfonium reagent, (2-ethoxy-1-fluoro-2-oxoethyl)(phenyl)(2,3,4,5-tetramethylphenyl)sulfonium tetrafluoroborate (1), serving as an effective alternative to the currently unknown 2-diazo-2-fluoroacetate ethyl transfer. This reagent applied Doyle-Kirmse cyclopropanation reactions operating under mild conditions with use earth-abundant metal catalysts. approach enables efficient valuable monofluorinated products.

Language: Английский

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