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Published on: August 16, 2018
Nickel-Catalyzed Remote Substitution of Alcohols
Zhi-Kai Zhang1,2, Jun-An Lu2, Shengye Zhang2
1College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, P. R. China.
Journal of the American Chemical Society
|May 14, 2026
Summary
This study introduces a novel nickel-catalyzed reaction for remote C-C bond formation in alkenyl alcohols. The method utilizes unprotected alcohols, enabling substitution at positions distant from the hydroxyl group.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Conventional substitution reactions require preactivation and occur at specific positions.
- Forming C-C bonds remote from functional groups is challenging.
- Direct utilization of native alcohols in remote substitution is underexplored.
Purpose of the Study:
- To develop a nickel-catalyzed method for remote substitution of unprotected alkenyl alcohols.
- To enable C-C bond formation at positions distal to the hydroxyl group.
- To overcome limitations of conventional substitution reactions.
Main Methods:
- Nickel-catalyzed reaction using arylboronic acids.
- Employing a bulky 1,3-diketone ligand to enhance nickel oxophilicity.
- Promoting selective β-OH elimination over β-H elimination.
Main Results:
- Successful remote C-C bond formation at positions distal to the hydroxyl group.
- Demonstrated regioselectivity and broad functional-group tolerance.
- Compatibility with various alkenyl alcohols under mild, redox-neutral conditions.
Conclusions:
- A novel and efficient strategy for remote substitution of unprotected alkenyl alcohols has been established.
- The developed method offers a powerful tool for complex molecule synthesis.
- This approach expands the scope of C-C bond formation strategies in organic chemistry.
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