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Mechanochemically Enabled Formal Reductive Cross-Coupling Reaction Between Aryl Ethers and Aryl Fluorides.
Tianfen Liu1, Xuemei Zhang1, Qingqing Wang1
1Department of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, Chengdu, 610041, P.R. China.
Angewandte Chemie (International Ed. in English)
|February 25, 2025
Summary
This study introduces a novel nickel-catalyzed reaction for synthesizing biphenyl compounds from aryl ethers and fluorides. The method works under mechanical conditions, overcoming challenges with sparingly soluble substrates and inactive bonds.
Area of Science:
- Organic Chemistry
- Materials Science
- Catalysis
Background:
- Reductive cross-coupling reactions are vital in synthetic chemistry.
- Existing methods often involve electrophilic reagents with zero or one inactive bond.
- Reactions using electrophilic reagents with two inactive bonds are underexplored.
Purpose of the Study:
- To develop the first nickel-catalyzed reductive cross-coupling reaction under mechanical conditions.
- To synthesize multifunctional biphenyl compounds using aryl ethers and aryl fluorides.
- To explore a new method for polymer degradation and luminescent material development.
Main Methods:
- Utilized nickel catalysis under mechanical (ball milling) conditions.
- Employed aryl ethers and aryl fluorides as electrophilic reagents with two inactive bonds.
- Conducted mechanistic studies involving nickel and magnesium activation of C─F bonds.
Main Results:
- Successfully synthesized various multifunctional biphenyl compounds.
- Demonstrated the efficacy of the reaction with sparingly soluble substrates, overcoming solvent limitations.
- Identified nickel and magnesium as key catalysts for C─F bond activation.
Conclusions:
- This work presents a pioneering nickel-catalyzed reductive cross-coupling of aryl ethers and fluorides under mechanical conditions.
- The developed method enables the synthesis of challenging biphenyl compounds and offers potential applications in polymer degradation and luminescent materials.
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