Ligand‐Enabled NiII‐Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen

Author:

Wang Dao‐Ming12,She Li‐Qin1,Yuan Hao1,Wu Yichen1,Tang Yong12,Wang Peng134ORCID

Affiliation:

1. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road Shanghai 200032 P. R. China

2. Chang-Kung Chuang Institute School of Chemistry and Molecular Engineering East China Normal University 500 Dongchuan Lu Shanghai 200062 P. R. China

3. 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

4. CAS Key Laboratory of Energy Regulation Materials Shanghai Institute of Organic Chemistry, CAS 345 Lingling Road Shanghai 200032 P. R. China

Abstract

AbstractThe 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.

Funder

National Natural Science Foundation of China

National Key Research and Development Program of China

Program of Shanghai Academic Research Leader

Publisher

Wiley

Subject

General Chemistry,Catalysis

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4. Comprehensive Organic Functional Group Transformations II Vol. 2 (Eds.: A. R. Katrinsky R. J. K. Taylor) Elsevier Amsterdam 2005.

5. For selected reviews on hydration of alkenes using Mukaiyama-type protocols

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