Origins of regioselectivity in Ni-catalyzed hydrofunctionalization of alkenes <i>via</i> ligand-to-ligand hydrogen transfer mechanism
Han Gao, Lingfei Hu, Yanlei Hu, Xiangying Lv, Yan‐Bo Wu, Gang Lü
Abstract
The origins of regioselectivity in Ni-catalyzed alkene hydrofunctionalizations were computationally investigated by using energy decomposition analysis. The results indicate the Markovnikov selectivity with aryl-substituted alkenes is favored due to the stabilizing charge transfer effect, and the anti-Markovnikov selectivity with alkyl-substituted alkenes is favored because of the destabilizing Pauli repulsion effect.
Topics & Concepts
Markovnikov's ruleRegioselectivityChemistryAlkeneSelectivityCatalysisLigand (biochemistry)AlkylMedicinal chemistryArylCombinatorial chemistryOrganic chemistryReceptorBiochemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis