Ni-Catalyzed Intermolecular C(sp<sup>3</sup>)–H Amidation Tuned by Bidentate Directing Groups
Yeong Bum Kim, Joonghee Won, Jeonghyo Lee, Jun-Ho Kim, Bingwei Zhou, Jung‐Woo Park, Mu‐Hyun Baik, Sukbok Chang
Abstract
We disclose herein a directing group-assisted nickel-catalyzed intermolecular C(sp3)–H amidation using organic azides as nitrene precursors. With the installation of an electronically tailored directing group, enhanced amidation efficiency was achieved. A series of experimental and computational studies suggested that a putative nickel(III)-nitrenoid species is a key intermediate in the C–N bond-forming process.
Topics & Concepts
NitreneIntermolecular forceCatalysisChemistryNickelDenticityCombinatorial chemistryStereochemistryMedicinal chemistryMoleculeOrganic chemistryMetalCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques