Nickel-catalyzed cross-coupling between benzyl alcohols and alkenyl triflates assisted by titanium-mediated radical C–O bond cleavage

Abstract A Ni-catalyzed radical cross-coupling reaction between benzyl alcohols and alkenyl triflates was discovered. A benzyl radical was generated directly from alcohols by using low-valent Ti-mediated alcohol C–O bond homolysis and was successfully utilized in a Ni-catalyzed cross-coupling reaction. The addition of tetrabutylammonium iodide (n-Bu4NI) facilitated the reaction. n-Bu4NI was found to be instrumental in transforming alkenyl triflates into iodides, which are more reactive in the subsequent cross-coupling process.