Ligand-Enabled NiII-Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen
Dao-Ming Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai, 200062 P. R. China
Search for more papers by this authorLi-Qin She
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorHao Yuan
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorDr. Yichen Wu
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorProf. Dr. Yong Tang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Peng Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 P. R. China
CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorDao-Ming Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai, 200062 P. R. China
Search for more papers by this authorLi-Qin She
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorHao Yuan
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorDr. Yichen Wu
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorProf. Dr. Yong Tang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Peng Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 P. R. China
CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032 P. R. China
Search for more papers by this authorGraphical Abstract
Ni-catalyzed hydroxylarylation of alkenes has been realized with highly efficient 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.
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.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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