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Iron-Catalyzed Multicomponent C–H Alkylation of in Situ Generated Imines via Photoinduced Ligand-to-Metal Charge Transfer

Pengcheng Li, Jia‐Lin Tu, Ao-Men Hu, Yining Zhu, Jiawen Yin, Lin Guo, Chao Yang, Wujiong Xia

2024Organic Letters18 citationsDOI

Abstract

Herein, we describe a novel photoinduced iron-catalyzed strategy for multicomponent C-H alkylation of in situ generated imines. By utilizing the alkyl radicals generated through iron-mediated photocatalytic C-H activation, the imines formed in situ are further subjected to addition reactions, resulting in the synthesis of various secondary and tertiary amine products. This method is simple to operate and does not require additional oxidants. It is applicable to inert alkane substrates such as cyclic alkanes, cyclic ethers, toluene, and ketones. The reaction is also compatible with various aromatic amines, alkyl amines, halogenated aromatic amines, as well as aromatic aldehydes, alkyl aldehydes, and cinnamaldehyde, among other different types of aldehydes.

Topics & Concepts

ChemistryAlkylationIn situCatalysisLigand (biochemistry)MetalCharge (physics)PhotochemistryCombinatorial chemistryOrganic chemistryReceptorQuantum mechanicsBiochemistryPhysicsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions
Iron-Catalyzed Multicomponent C–H Alkylation of in Situ Generated Imines via Photoinduced Ligand-to-Metal Charge Transfer | Litcius