Iron-Catalyzed Alkoxyl Radical-Induced C-C Bond Cleavage/gem-Difluoroalkylation Cascade

An inexpensive iron-catalyzed alkoxylradical-inducedC-Cbond cleavage/gem-difluoroalkylation cascade is presented.Regulated by the structure of alkoxyl radical precursors, fluorinateddistal diketones were synthesized through a ring-opening strategyand difluoroalkylated medium-sized lactones and macrolactones wereconstructed via a ring-expansion strategy. Both protocols proceededunder mild and redox neutral conditions with a broad substrate scopeand good functional group compatibility.

Automated summary

An inexpensive iron-catalyzed alkoxylradical-induced C-C bond cleavage/gem-difluoroalkylation cascade is developed. Fluorinated distal diketones are synthesized via a ring-opening strategy regulated by the structure of alkoxyl radical precursors, while difluoroalkylated medium-sized lactones and macrolactones are constructed through a ring-expansion strategy. Both protocols show mild and redox neutral conditions, broad substrate scope, and good functional group compatibility.