Deoxazole is an N-heterocyclic carbene salt which activates free alcohols for a C-C cross coupling reaction with aryl halides. The MacMillan group developed a mild, robust, and selective metallaphotoredox-based cross-coupling platform for the deoxygenative coupling for free alcohols using Deoxazole, a Ni catalyst, and [Ir(dtbbpy)(ppy)₂]PF₆.