Based on these observations, a plausible catalytic cycle involving an ECEC sequence is depicted in Figure . Anodic oxidation of the Co II complex and cathode reduction of methanol would afford Co III and methoxide anion, respectively. Hydride exchange between the silane and Co III could be facilitated by methoxide. The resulting Co-H species 21 would undergo HAT with an alkene to afford an alkyl radical 22, followed by Co II trapping to give an alkylcobalt(III) complex 23. A second anodic oxidation then takes place to convert 23 to a highly electrophilic Co IV complex 24, which would be rapidly intercepted by a nucleophile next to the anode to form the hydrofunctionalization product 25 and regenerate the Co II complex. The major side pathways include reduction (hydrogenation) and isomerization. The latter could be a result of either back-HAT from the alkyl radical to Co II and/or the deprotonation of Co IV complex 24.