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Rhodium-Catalyzed Pyridine Assisted C-H Arylation for the Synthesis of Planar Chiral Ferrocenes
CCS Chemistry ( IF 9.4 ) Pub Date : 2020/5/15 , DOI: 10.31635/ccschem.020.202000157
Chen-Xu Liu 1 , Zhong-Jian Cai 1 , Qiang Wang 1 , Zhi-Jie Wu 1 , Qing Gu 1 , Shu-Li You 1
Affiliation  

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 catalyst.

中文翻译:

铑催化的吡啶辅助的CH芳基化反应合成平面手性二茂铁

平面手性二茂铁广泛用于有机合成,材料科学和药物化学中,但合成并不简单。本文中,开发了通过Rh(I)催化的吡啶基二茂铁与芳基卤化物的直接偶联,高效合成平面手性二茂铁基吡啶衍生物。对于多种底物,均具有良好的产率和出色的对映选择性(95-> 99%ee)。克级合成和较低的催化剂负载量(基于[Rh]低至1 mol%)的相容性增强了当前方法的实用性。产生的偶联产物可以容易地转化为手性配体。机理研究表明,吡啶基二茂铁的C–H键裂解可能是可逆的步骤,而不是速率决定步骤。
更新日期:2020-12-18
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