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Solvent-Switched Manganese(I)-Catalyzed Regiodivergent Distal vs Proximal C–H Alkylation of Imidazopyridine with Maleimide

Subhendu Ghosh, Tamanna Khandelia, Bhisma K. Patel

2021Organic Letters50 citationsDOI

Abstract

A sustainable Mn(I)-catalyzed exclusive solvent-dependent functionalization of imidazopyridine with maleimide via an electrophilic metalation at the distal (in 2,2,2-trifluoroethanol (TFE)) and chelation assisted at the proximal (in tetrahydrofuran (THF)) has been developed. The strategy was successfully applied to the drug Zolimidine and a broad range of substrates, thereby reflecting the method's versatility.

Topics & Concepts

ImidazopyridineChemistryMaleimideMetalationTetrahydrofuranElectrophileCatalysisSolventAlkylationManganeseCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis
Solvent-Switched Manganese(I)-Catalyzed Regiodivergent Distal vs Proximal C–H Alkylation of Imidazopyridine with Maleimide | Litcius