Visible-Light Promoted Selective Imination of Unactivated C–H Bonds via Copper-nitrene Intermediates for the Synthesis of 2H‑Azirines
journal contributionposted on 04.10.2019, 13:34 by Liyan Feng, Chao Yang, Wujiong Xia
A novel strategy to trap iminyl radicals with copper ions has been developed at room temperature, the resulted high-valent Cu(III) imine intermediate resets quickly to form nitrene and then to furnish a 2H-azirine. This protocol with dual copper/photoredox catalyst enables the selective imination of unactivated C–H bonds under mild conditions with a broader scope. Moreover, this method also uncovers a novel ring-expansion rearrangement from cyclobutyl oxime derivatives to give the α-acylamino cyclopentanones.
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α- acylamino cyclopentanonesazirinenovel strategycopper ionsiminetrap iminyl radicalsscopeform nitrenemethodhigh-valentSynthesiUnactivatedcyclobutyl oxime derivativesIminationcatalystnovel ring-expansion rearrangementCopper-nitrene IntermediatesBondresetunactivatedVisible-Light PromotediminationAzirineroom temperature2 HuncoverCubond