Substitution reaction

Radical

Physical chemistry

Catalysis

Electrode

Homolysis

Organic chemistry

Chemistry

Combinatorial chemistry

Ferrocene

Alkyne

Ring (chemistry)

Reagent

Electrochemistry

Photochemistry

Journal of the American Chemical Society

An unprecedented radical difluoromethylarylation reaction of alkynes has been developed by discovering a new difluoromethylation reagent, CF2HSO2NHNHBoc. This air-stable and solid reagent can be prepared in one step from commercially available reagents CF2HSO2Cl and NH2NHBoc. The CF2H radical, generated through ferrocene-mediated electrochemical oxidation, participates in an unexplored alkyne addition reaction followed by a challenging 7-membered ring-forming homolytic aromatic substitution step to afford fluorinated dibenzazepines.

Electrochemical Difluoromethylarylation of Alkynes