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Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis
Zhi-Chao Cao1, Qin-Yu Luo1, Zhang-Jie Shi1,2
1Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Green Chemistry Centre, Peking University , Beijing 100871, China.
Organic Letters
|December 10, 2016
Summary
Nickel-catalyzed C-O activation enables cross-coupling of aryl bromides with diverse O-based electrophiles, including phenols. This environmentally friendly method offers broad substrate scope and requires low catalyst loading.
Area of Science:
- Organic Chemistry
- Catalysis
- Sustainable Chemistry
Background:
- Cross-coupling reactions are fundamental in organic synthesis.
- C-O bond activation presents a significant challenge in catalysis.
- Developing efficient methods for coupling O-based electrophiles is crucial.
Purpose of the Study:
- To develop a novel nickel-catalyzed method for C-O activation.
- To achieve cross-coupling of various O-based electrophiles with aryl bromides.
- To explore the reactivity of phenols in this transformation.
Main Methods:
- Nickel-catalyzed C-O activation.
- Utilizing magnesium as a promoter.
- Employing various O-based electrophiles including carboxylates, carbamates, ethers, and phenols.
Main Results:
- Successful cross-coupling of aryl bromides with diverse O-based electrophiles.
- Phenols demonstrated excellent reactivity under modified conditions.
- The reaction proceeded with low catalyst loading and easy manipulation.
- Broad substrate scope was observed.
Conclusions:
- A simple and environmentally benign cross-coupling method was established.
- The developed chemistry offers a versatile approach for C-O bond formation.
- This method expands the scope of nickel-catalyzed cross-coupling reactions.
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