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Ligand‐Enabled Ni <sup>II</sup> ‐Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen

Dao‐Ming Wang, Li‐Qin She, Hao Yuan, Yichen Wu, Yong Tang, Peng Wang

2023Angewandte Chemie International Edition14 citationsDOIOpen Access PDF

Abstract

The use of molecular oxygen as the terminal oxidant in transition metal catalyzed oxidative process is an appealing and challenging task in organic synthetic chemistry. Here, we report a Ni-catalyzed hydroxylarylation of unactivated alkenes enabled by a β-diketone ligand with high efficiency and excellent regioselectivity employing molecular oxygen as the oxidant and hydroxyl source. This reaction features mild conditions, broad substrate scope and incredible heterocycle compatibility, providing a variety of β-hydroxylamides, γ-hydroxylamides, β-aminoalcohols, γ-aminoalcohols, and 1,3-diols in high yields. The synthetic value of this methodology was demonstrated by the efficient synthesis of two bioactive compounds, (±)-3'-methoxyl citreochlorol and tea catechin metabolites M4.

Topics & Concepts

CatalysisRegioselectivityChemistryMolecular oxygenLigand (biochemistry)Combinatorial chemistrySubstrate (aquarium)OxygenTransition metalGreen chemistryOrganic chemistryReaction mechanismReceptorBiochemistryOceanographyGeologyOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions