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Enantioselective C2–H Alkylation of Pyridines with 1,3-Dienes via Ni–Al Bimetallic Catalysis

Jiang‐Fei Li, Deng Pan, Hao-Rui Wang, Tao Zhang, Yi Li, Genping Huang, Mengchun Ye

2022Journal of the American Chemical Society82 citationsDOI

Abstract

A chiral phosphine oxide-ligated Ni-Al bimetallic catalyst was used to realize an enantioselective C2-H alkylation of pyridines without the need of a C2-block. A wide range of pyridines, including unsubstituted pyridine, C3, C4, and C2-substituted pyridines, and even complex pyridine-containing bioactive molecules are well compatible with the reaction, providing up to 81% yield and up to 97% ee.

Topics & Concepts

ChemistryAlkylationEnantioselective synthesisBimetallic stripPyridineCatalysisYield (engineering)PhosphinePhosphine oxideOrganic chemistrySynergistic catalysisMedicinal chemistryCombinatorial chemistryMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis
Enantioselective C2–H Alkylation of Pyridines with 1,3-Dienes via Ni–Al Bimetallic Catalysis | Litcius