Light Promoted Vinylogous Arbuzov Reaction with Electron Deficient Alkyl Halides

A vinylogous radical Arbuzov reaction involving the coupling of alkyl halides, terminal acetylenes, and triethyl phosphite furnishing vinyl phosphonates is described. Fluorinated iodides and α-bromoesters served as sources of radicals. The reaction is initiated by 400 nm light with or without photocatalyst, depending on the alkyl halide. The fluoroalkylation products could be further partially protodefluorinated using 1,3,5-trimethyltriazinane.