Synthesis of Diverse γ-Lactams via Rh-Catalyzed C(sp<sup>2</sup>)–H Addition to Aliphatic Nitriles
Wen‐Wei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing‐Yuan Ge, Ningning Lv, Jiuxi Chen
Abstract
We herein report an unprecedented pathway to access γ-lactams using acetonitrile analogues as coupling partners without oxidants, ligands, and Lewis acids. The reaction undergoes Rh-catalyzed C(sp2)–H addition to carbon-bound nitriles with the aid of an amide traceless auxiliary followed by an annulation sequence, featuring a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations highlight the potential synthetic utility of this methodology. A plausible mechanism is proposed based on mechanistic investigations.
Topics & Concepts
ChemistryCatalysisCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions