Divergent defluorocarboxylation of & alpha;-CF3 alkenes with formate via photocatalyzed selective mono- or triple C-F bond cleavage

Unprecedented divergent synthesis of gem-difluorovinylacetic acid and glutaric acid derivatives from & alpha;-CF3 alkenes with formate as the carbonyl source was disclosed. The reaction can undergo selective mono- or triple C-F bond cleavage by simply switching the photocatalyst and hydrogen atom transfer (HAT) catalyst under visible-light-induced conditions at room temperature. Foramte acts as both the C1 source and the reductant through the generation of CO2 & BULL;- species, which underwent Giese radical addition to electron-deficient alkenes to trigger the consecutive C-F bond cleavage and carboxylation process.

Automated summary

An unprecedented divergent synthesis of gem-difluorovinylacetic acid and glutaric acid derivatives from α-CF3 alkenes using formate as the carbonyl source was discovered. The reaction can selectively undergo mono- or triple C-F bond cleavage by switching the photocatalyst and HAT catalyst under visible-light-induced conditions at room temperature. Formate serves as both the C1 source and reductant, generating CO2? species that undergo Giese radical addition to electron-deficient alkenes, triggering consecutive C-F bond cleavage and carboxylation processes.