Catalytic C–H Bond Alkylation of Azoles with Alkyl Halides Mediated by Nickel(II) Complexes of Phenanthridine-Based <i>N</i>^<i>N</i><sup><i>–</i></sup>^<i>N</i> Pincer Ligands
Pavan Mandapati, Jason D. Braun, Baldeep K. Sidhu, Gabrielle Wilson, David E. Herbert
Abstract
Ni(II) complexes supported by tridentate N^N–^N diarylamido pincer-type ligands have been demonstrated to act as active catalysts in the carbon–carbon bond forming alkylation of azoles using unactivated alkyl halides. Here, we show that benzannulated phenanthridine-containing ligands can form homogeneous Ni(II) catalysts active with both benzoxazole and benzothiazole substrates. These precatalysts have been fully characterized in solution and the solid state, including by cyclic voltammetry.
Topics & Concepts
ChemistryBenzoxazolePincer movementAlkylationBenzothiazoleMedicinal chemistryAlkylCatalysisPhenanthridineNickelHalideOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions