Radical trifluoromethoxylation of fluorinated alkenes for accessing difluoro(trifluoromethoxy)methyl groups.

ABSTRACT: In this study, we explore the potential of the difluoro(trifluoromethoxy)methyl group, CF₂-O-CF₃, an underexplored but promising structural analog of the trifluoromethoxy group (OCF₃). This moiety offers unique electronic properties and enhanced chemical stability due to its multiple C-F bonds, along with the added advantage of C-O bond cleavage, making it an attractive option in fluorine chemistry. We have succeeded in synthesizing difluoro(trifluoromethoxy)methyl compounds via radical amino- and hydroxy-trifluoromethoxylations of β,β-difluorostyrenes. Control experiments, including radical clock experiments, support a free radical mechanism. The synthetic utility of the resulting difluoro(trifluoromethoxy)methyl compounds is also demonstrated throu

SUBMITTER: Kawai K 

PROVIDER: S-EPMC11726583 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature