A photocatalytic sp3 C-S, C-Se and C-B bond formation through C-C bond cleavage of cycloketone oxime estersElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ob02987c

The photocatalytic thiolation, selenylation and borylation of cycloketone oxime esters through iminyl radical-triggered C-C bond cleavage were described. The reactions provide a unified approach to alkyl sulfur, selenium and boron compounds tethered to a synthetically useful nitrile group. The photocatalytic sulfuration, selenylation and borylation of cycloketone oxime esters through iminyl radical-triggered C-C bond cleavage were described. The reactions provide a unified approach to alkyl sulfur, selenium and boron compounds tethered to a synthetically useful nitrile group.