Ligand-Enabled NiII -Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen
Dao-Ming Wang1,2, Li-Qin She1, Hao Yuan1
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.
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.
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