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The Merger of Halogen Atom Transfer (XAT) and Energy Transfer Catalysis (EnT) for the Modular 1,2-Iminylalkylation of Diazenes

Shanshan Li, Yu‐Shi Jiang, Li-Ning Chen, Danna Chen, Xue-Ling Luo, Cheng‐Xue Pan, Peng‐Ju Xia

2023Organic Letters25 citationsDOI

Abstract

The 1,2-iminylalkylation of diazenes using alkyl iodides in combination with an O -benzoyl oxime is reported. In this transformation, O -benzoyl oxime acted as a radical precursor and XAT mediator. In addition to common alkyl iodides, other alkyl iodides such as iodomethane, iodomethane- d 3, trifluoroiodomethane, ethyl difluoroiodoacetate, and iodoalkanes containing unprotected hydroxyl and amide groups can also serve as C-radical precursors in the 1,2-iminylalkylation with electrophilic diazenes as radical acceptors.

Topics & Concepts

ChemistryAlkylHalogenElectrophileCatalysisOximeAmideMedicinal chemistryHalogenationOrganic chemistryCombinatorial chemistryOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
The Merger of Halogen Atom Transfer (XAT) and Energy Transfer Catalysis (EnT) for the Modular 1,2-Iminylalkylation of Diazenes | Litcius