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Transalkylation via C–N Bond Cleavage of Amines Catalyzed by Super Organophotoreductant CBZ6

Yong-Ze Chen, Yiming Chen, Yuan Hu, Jian‐Ping Qu, Yan‐Biao Kang

2023Organic Letters17 citationsDOI

Abstract

The super organoreductant CBZ6-catalyzed tandem transalkylation-cyclization using amines as traceless radical donors and stabilizer is reported. The later-stage breaking of an N-C bond enables the transalkylation with a secondary amine as the leaving moiety. A wide range of tertiary amines were used as alkyl radical donors for the C1-C8 alkyls. This traceless stabilizer also enabled the transalkylation with methyl radical, which is normally not possible because of the instability of methyl radical.

Topics & Concepts

TransalkylationChemistryMoietyTandemCatalysis2-Norbornyl cationAmine gas treatingBond cleavageMedicinal chemistryCleavage (geology)Tertiary amineAnilineAlkylAlkylationOrganic chemistryMaterials scienceGeotechnical engineeringFracture (geology)Composite materialEngineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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