Photochemically Enabled, Ni-Catalyzed Cyanation of Aryl Halides
Yonggang Yan, Jinjin Sun, Gang Li, Liu Yang, Wei Zhang, Rui Cao, Chao Wang, Jianliang Xiao, Dong Xue
Abstract
A light-promoted Ni-catalyzed cyanation of aryl halides employing 1,4-dicyanobenzene as a cyanating agent is reported. A broad array of aryl bromides, chlorides, and druglike molecules could be converted into their corresponding nitriles (65 examples). Mechanistic studies suggest that upon irradiation, the oxidative addition product Ni(II)(dtbbpy)(p-C6H4CN)(CN) undergoes homolytic cleavage of the Ni–aryl bond to generate an aryl radical and a Ni(I)–CN species, the latter of which initiates subsequent cyanation reactions.
Topics & Concepts
CyanationChemistryArylHomolysisHalideCatalysisBond cleavagePhotochemistryMedicinal chemistryOxidative additionCleavage (geology)MoleculeCombinatorial chemistryOrganic chemistryRadicalGeotechnical engineeringFracture (geology)EngineeringAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques