Silver-Catalyzed Carbofluorination of Olefins and α-Fluoroolefins with Carbamoyl Radicals

Émilie Vincent; Julien Brioche

doi:10.1002/chem.202401419

Silver-Catalyzed Carbofluorination of Olefins and α-Fluoroolefins with Carbamoyl Radicals

Chemistry. 2024 May 7:e202401419. doi: 10.1002/chem.202401419. Online ahead of print.

Authors

Émilie Vincent¹, Julien Brioche²

Affiliations

¹ Université de Rouen, Department of Chemistry, Univ Rouen Normandie, INSA Rouen Normandie, CNRS, Normandie Univ,, COBRA UMR 6014, INC3M FR 3038, 76000, Rouen, FRANCE.
² Universite de Rouen, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), Normandie Univ, Bât. IRCOF (no 40), 76000, Rouen, FRANCE.

PMID: 38712694
DOI: 10.1002/chem.202401419

Abstract

The reactivity of carbamoyl radicals, generated in situ from sodium oxamate salts, has been investigated in the context of radical carbofluorination reactions of olefins and a-fluoroolefins, respectively. Both transformations are catalyzed by silver salts and required the presence of potassium persulfate (K2S2O8) and SelectfluorTM as a radicophilic fluorine source. The reported methods provide a direct access to beta-fluoroamides and beta,beta-difluoroamides.

Keywords: Carbamoyl Radicals; Fluorine chemistry; Radical Carbofluorination; β,β-Difluoroamide; β-Fluoroamide.