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A highly efficient synthesis of planar chiral ferrocenylpyridine derivatives via Pd-catalyzed intramolecular C-H arylation was developed, and quantitative yields and excellent enantioselectivity were obtained for a wide range of substrates. Notably, the catalyst loading could be lowered to 0.2 mol %, which represents the highest catalytic efficiency found for asymmetric C-H bond activation (TON up to 495). These compounds could be easily transformed to pyridine N-oxides, displaying promising catalytic reactivity in the asymmetric opening of meso-epoxide. Moreover, computational investigations were conducted to clarify the origin of the excellent enantioselectivity. The compatibility of large-scale synthesis and low catalyst loading should enhance the practicality of the synthetic application of the current method.
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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion