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Published on: November 9, 2019
Ball-milling-mediated remote asymmetric reductive coupling in air
Hao Lei1,2,3, Yufang Yang4, Jiajia Sun4
1College of Applied Sciences, Shenzhen University, Shenzhen 518060, China.
This study introduces a novel mechanochemical method for asymmetric three-component radical reductive coupling. This approach enables efficient synthesis of complex molecules with high yields and enantioselectivity, advancing green chemistry in asymmetric synthesis.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Catalysis
Background:
- Dicarbofunctionalization of unsaturated systems via radical relay is vital for complex molecule synthesis.
- Mechanochemistry offers sustainable advantages over traditional solvent-based reactions.
- Catalytic asymmetric versions of solid-state cross-coupling reactions are underdeveloped.
Purpose of the Study:
- To develop a mechanochemical protocol for asymmetric three-component radical reductive coupling.
- To establish a nickel-catalyzed asymmetric reductive cross-coupling under mechanochemical conditions.
- To expand the scope of asymmetric synthesis in mechanochemistry.
Main Methods:
- Utilized a mechanochemical approach for solid-state reactions.
- Employed a nickel catalyst for asymmetric radical reductive coupling.
- Investigated a three-component coupling strategy.
Main Results:
- Achieved moderate to excellent yields (49%-88%) for target products.
- Obtained high enantioselectivities, up to 90%.
- Demonstrated the first nickel-catalyzed asymmetric reductive cross-coupling under mechanochemical conditions.
Conclusions:
- The developed protocol is effective for asymmetric three-component radical reductive coupling.
- This work represents a significant advancement in mechanochemical asymmetric synthesis.
- The findings open new avenues for sustainable and efficient synthesis of chiral molecules.
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