Rhodium-catalyzed pyridine-assisted C–H arylation for the synthesis of planar chiral ferrocenes

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Abstract

Planar chiral ferrocenes are widely applied in organic synthesis, materials science, and medicinal chemistry, but their synthesis is not trivial. Herein, a highly efficient synthesis of planar chiral ferrocene-based pyridine derivatives via Rh(I)-catalyzed direct coupling of pyridylferrocenes with aryl halides was developed. Good yields and excellent enantioselectivity (95–>99% ee) are obtained for a wide range of substrates. The compatibility of gram-scale synthesis and relatively low catalyst loading (down to 1 mol% based on [Rh]) enhance the practicality of the current method. The generated coupling products can be readily transformed into chiral ligands. Mechanistic studies suggest that the C–H bond cleavage of pyridylferrocene may be a reversible step and not the rate-determining step. Significant nonlinear effects indicate the existence of multiple metals or ligands in the active.

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Liu, C. X., Cai, Z. J., Wang, Q., Wu, Z. J., Gu, Q., & You, S. L. (2020). Rhodium-catalyzed pyridine-assisted C–H arylation for the synthesis of planar chiral ferrocenes. CCS Chemistry, 2(6), 642–651. https://doi.org/10.31635/ccschem.020.202000157

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