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Ligand Relay Catalysis Enables Asymmetric Migratory Reductive Acylation of Olefins or Alkyl Halides

Xiaoli Jiang, Feng‐Tao Sheng, Yao Zhang, Gao Deng, Shaolin Zhu

2022Journal of the American Chemical Society92 citationsDOI

Abstract

Design of ligands in transition-metal catalyzed reactions is challenging, especially in asymmetric transformations. With each step in the catalytic cycle promoted by its privileged ligand and different steps well-connected by dynamic ligand exchange, synergistic combination of multiple ligands could potentially enhance the catalytic efficiency and selectivity. Now, this concept has been applied to the NiH-catalyzed asymmetric remote hydroacylation of olefins and migratory acylation of alkyl halides with excellent regio- and enantioselectivity, utilizing two simple ligands, one for chain-walking and the other for asymmetric acylation. Starting from abundant alkenes/alkyl halides and carboxylic acids, a wide range of enantioenriched chiral α-aryl ketones can be efficiently accessed under mild conditions.

Topics & Concepts

ChemistryAcylationAlkylLigand (biochemistry)HalideCatalysisMigratory insertionCombinatorial chemistryCatalytic cycleArylEnantioselective synthesisReductive eliminationSelectivityOrganic chemistryReceptorBiochemistryAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
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