Solid-state synthesis of BINOLs by copper-based catalysis Farshid Effaty 1,2 , Patrick A. Julien 1 , Xavier Ottenwaelder* 2 , Tomislav Friščić* 1 1 Chemistry Department, McGill University, Canada, 2 Chemistry and Biochemistry Department, Concordia University, Canada Mechanochemical reactions, particularly those involving ball milling, are increasingly being investigated as a means of achieving greener, more efficient, and novel reactivity in the absence of bulk solvents. Catalytic milling reactions have received few reports, and their reactivity is poorly understood.[1] The mechanochemical synthesis of 1,1-bi-2-naphthol (BINOL) and derivatives, a versatile family of ligands used in a wide range of metal-based and organocatalytic systems, is presented here. The presentation will specifically describe a catalytic mechanochemical approach for the synthesis of BINOL via a copper-catalyzed C-H activation and compare it to previously reported solution reactivity. The results show that mechanochemical synthesis of BINOL can proceed faster and at lower temperatures than equivalent solution syntheses, while also providing an excellent model for fundamental studies of the behavior of catalytic milling reactions of crystalline solids, based on real-time monitoring using in situ techniques such as powder X-ray diffraction and hot-stage microscopy. References 1. M. Nakajima, S. Hashimoto, M. Noji, and K. Koga, “Aerobic Oxidative Coupling of 2-Naphthol Derivatives Catalyzed by a Copper-Amine Complex without Solvent,” Chem. Pharm. Bull. , 1998 , 46 . 1814-1815.
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