Palladium-Catalyzed <i>meta</i>-Selective C–H Functionalization by Noncovalent H-Bonding Interaction
Guoshuai Li, Yifei Yan, Pengfei Zhang, Xiaohua Xu, Zhong Jin
Abstract
Controlling positional selectivity represents one of the most important aspects in transition-metal-catalyzed C–H bond functionalization. However, the conventional directing template strategies via a covalent binding to the substrates are always hindered by prior stoichiometric installation and removal of the directing groups. Herein, we report a palladium-catalyzed meta-selective C–H olefination of aromatic carbonyl compounds by noncovalent hydrogen-bonding interaction. N,N′-Substituted ureas were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group.
Topics & Concepts
PalladiumSurface modificationCatalysisChemistryCovalent bondHydrogen bondNon-covalent interactionsCombinatorial chemistrySelectivityStoichiometryOrganic chemistryMoleculePhysical chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques