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Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

Xiao Cheng, Bao‐Gui Cai, Hui Mao, Juan Lü, Lei Li, Kun Wang, Jun Xuan

2021Organic Letters78 citationsDOI

Abstract

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.

Topics & Concepts

ImidazolidineAziridineChemistryDiazoYield (engineering)PhotochemistryCycloadditionCombinatorial chemistryBlue lightIrradiationVisible spectrumCatalysisOrganic chemistryOptoelectronicsPhysicsRing (chemistry)MetallurgyMaterials scienceNuclear physicsCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods