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Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives

Yong Deng, Shiqi You, Mengyao Ruan, Ying Wang, Zuxing Chen, Guichun Yang, Meng Gao

2020Advanced Synthesis & Catalysis29 citationsDOI

Abstract

Abstract The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines. magnified image

Topics & Concepts

ChemistryIndole testRegioselectivityElectrochemistryCombinatorial chemistryPhosphorylationCatalysisSurface modificationElectrolyteOrganic chemistryElectrodeBiochemistryPhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives | Litcius