We report a one-pot, direct C-H functionalization reaction of alkenes mediated by [CpCo(NO)(2)]. All intermediates in the proposed reaction sequence have been characterized. A variety of Michael acceptors can be utilized with the one-pot procedure to give the desired cyclic tetraalkyl-substituted, gamma,delta-unsaturated compounds in good yields. We also provide a preliminary result for catalytic turnover in both base and [CpCo(NO)(2)].