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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Air-Stable Organoradical Boron Reagents
Zenghui Li1, Jing Wang1, Xiaoyang Liu2
1School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi An Shi, Xi'an, 710049, China.
Researchers synthesized novel organoradical boron reagents using direct C-H borylation, enabling new functional materials. These stable radical compounds are useful in Suzuki-Miyaura coupling and for creating luminescent materials.
Area of Science:
- Organic Chemistry
- Materials Science
Background:
- Organic radicals and organoboron reagents are widely studied independently.
- Direct C-H borylation of organic radicals to form building blocks has not been previously achieved.
Purpose of the Study:
- To synthesize novel organoradical boron reagents.
- To investigate their stability, properties, and reactivity.
- To explore their potential applications in synthesis and materials science.
Main Methods:
- Direct C-H borylation of TTM-H radical.
- Synthesis of TTM-Bpin and TTM-BOH reagents.
- Single crystal X-ray diffraction, Electron Paramagnetic Resonance (EPR) spectroscopy, and Density Functional Theory (DFT) calculations.
- Suzuki-Miyaura coupling (SMC) reactions.
Main Results:
- Successfully synthesized novel organoradical boron reagents (TTM-Bpin, TTM-BOH) via C-H borylation.
- These reagents exhibit good air stability for storage.
- Demonstrated successful Suzuki-Miyaura coupling with retention of the radical center.
- Observed fluorescent properties in the radical species.
Conclusions:
- Established a new method for creating organoradical boron building blocks.
- Developed stable, fluorescent radical compounds with potential for diverse applications.
- Opened avenues for synthesizing luminescent organic radicals and functional open-shell materials.
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