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Decarboxylative C–H Alkylation of Heteroarene <i>N</i>-Oxides by Visible Light/Copper Catalysis

Duanyang Liu, Xu Liu, Yan Gao, Chaoqun Wang, Jie‐Sheng Tian, Teck‐Peng Loh

2020Organic Letters29 citationsDOI

Abstract

This paper reports a highly site-selective alkylation of heteroarene N-oxides using hypervalent iodine(III) carboxylates to serve as an alkylating agent in the presence of a cheap copper catalyst under visible light conditions. This mild method proceeds at room temperature in an air atmosphere and can withstand various heteroarene N-oxides as well as various primary, secondary, and tertiary alkyl carboxylic acids. It also provides a practical method for enabling the rapid conversion of commercially available raw materials into medically relevant “drug-like” molecules.

Topics & Concepts

ChemistryAlkylationCopperCatalysisVisible spectrumOrganic chemistryCombinatorial chemistryMedicinal chemistryOptoelectronicsPhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions
Decarboxylative C–H Alkylation of Heteroarene <i>N</i>-Oxides by Visible Light/Copper Catalysis | Litcius