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IBX-Promoted Oxidative Cyclization of <i>N</i>-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines

Peng Gao, Huaijuan Chen, Zijing Bai, Mi‐Na Zhao, De‐Suo Yang, Juan Wang, Ning Wang, Lele Du, Zheng‐Hui Guan

2020The Journal of Organic Chemistry30 citationsDOI

Abstract

-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.

Topics & Concepts

ChemistryAldehydeReagentEnvironmentally friendlyAlcoholOrganic chemistrySubstrate (aquarium)Oxidative phosphorylationEnamineCombinatorial chemistryCondensationCondensation reactionSelectivityMetalCatalysisThermodynamicsOceanographyBiochemistryPhysicsGeologyEcologyBiologyOxidative Organic Chemistry ReactionsSynthesis and Characterization of PyrrolesCatalytic C–H Functionalization Methods