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Heat-Induced Granular Motion in Quasi-Solid-State Suzuki-Miyaura Reaction
Boško Vrbica1,2, Zhenzhong Zhang1, Abhijit Sen1
1RIKEN Center for Sustainable Resource Science (CSRS), Wako, Saitama, Japan.
This study introduces a novel, green solid-state Suzuki-Miyaura cross-coupling reaction. It avoids mechanical force, using heat-induced motion for efficient synthesis of complex materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Green Chemistry
Background:
- Solid-state cross-coupling offers sustainable synthesis routes but faces challenges with insoluble materials and harsh conditions.
- Existing methods often require significant mechanical force, limiting their applicability and real-time analysis.
Purpose of the Study:
- To develop a mild, additive-free, solid-state cross-coupling method that bypasses mechanical force.
- To enable the synthesis of insoluble polycyclic aromatic hydrocarbons and functional materials under green conditions.
Main Methods:
- A polymeric palladium-catalyzed quasi-solid-state Suzuki-Miyaura reaction was developed, relying on heat-induced convection for mass transfer.
- The reaction proceeded without external mechanical input, utilizing granular motion driven by thermal gradients.
Main Results:
- Various polycyclic aromatic hydrocarbons and functional materials were synthesized with yields up to 93%.
- Low palladium (Pd) loadings (500 mol ppm) were effective, and gram-scale synthesis of dinaphthyl anthracene was achieved.
- In-situ monitoring identified a boronate intermediate and revealed a granular motion mechanism.
Conclusions:
- The quasi-solid-state reaction offers a green and efficient alternative for synthesizing complex organic materials.
- The absence of mechanical force facilitates real-time analysis and mechanistic studies of solid-state reactions.
- This approach paves the way for scalable, sustainable synthesis of advanced materials.
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