"This method uses unfunctionalized aromatics such as benzene and toluene, which are inexpensive and readily available," said Hideo Ito of Nagoya University's Graduate School of Science. "By forming carbon-to-carbon bonds directly from these inert compounds, we reduce both the complexity and the cost of producing essential materials."
PAHs are valued for their stability and tunable properties. By extending research on aromatic ring coupling, the team successfully fused entire rings together-allowing for more intricate molecular architectures that have applications in electronics, dyes, and medicine.
Ito emphasized the importance of innovation in their success. "Many researchers failed to achieve this reaction in solution, and I imagine no one considered trying it in the solid state," he noted. "My student, Yoshifumi Toyama, took a chance using a ball mill, lithium metal, and fluorobenzene-and the reaction succeeded."
The technique, termed "C-C bond-forming aromatic electrophilic substitution (SNAr)-type Birch reductive arylation via the mechanochemical anionic activation of unfunctionalized PAHs," employs a solvent-free grinding method. This high-energy process triggers a Birch-type reduction and an SNAr-like mechanism, facilitating efficient electron transfer and ring fusion.
"Lithium reduces the PAH to an electron-rich nucleophile," Ito explained. "When it encounters electron-deficient fluoroarenes, a new C-C bond forms as the fluorine is displaced, creating complex biaryl structures."
The resulting biaryls are crucial to manufacturing pharmaceuticals and organic materials. With this method, producing such compounds becomes not only more effective but also environmentally friendlier.
Research Report:Birch reductive arylation by mechanochemical anionic activation of polycyclic aromatic compounds
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