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An efficient Co-catalyzed hydro-difluoromethylthiolation/hydro-trifluoromethylthiolation reaction of unactivated alkenes was described. Both reactions were conducted at room temperature and a variety of common functional groups such as halogen, ester, aldehyde, enolizable ketone or ester, nitro or cyano group, sulfonate and carbamate were compatible with the reaction conditions. Radical cyclization and radical inhibitor experiments suggested that the reaction proceeds through a free radical process. Image 1 [ABSTRACT FROM AUTHOR]

• Fluoroalkylthiol substituted 2,3-dihydrobenzofurans (DHB) was prepared in high to excellent yield under the irradiation of visible light. Various functional groups were tolerated. Fluorescence quenching experiment indicated that both oxidative and reductive quenching cycles occurred. And the reductive quenching was dominant. Difunctionalization of alkenes represent a convenient way to complex molecular structure. Herein, visible light-induced intramolecular carbodi(tri)fluoromethylthiolation of alkenes was reported. C C and C-S were formed in the procedure. Various fluoroalkylthiol substituted 2,3-dihydrobenzofurans (DHB) was prepared. Aryldiazonium salts derived from o-allyloxy anilines were used as precursors of aryl radicals. The following cyclization occurred, and the resulting alkyl radicals were trapped by shelf-stable reagent PhSO 2 SR f (R f = SCF 2 H, SCF 3). The direct difluoromethylthiolation on arenes was not observed. A variety of atoms and functional groups were tolerated. [Display omitted] A visible light-induced intramolecular carbodi(tri)fluoromethylthiolation of alkenes was reported, through which C C and C-S were formed with good functional group tolerance and yields. [ABSTRACT FROM AUTHOR]