The Journal of Organic Chemistry · 2019 · 33 citations · 71 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryAmino Acid ChemistryCatalytic MechanismsCross-coupling ReactionsLate-stage FunctionalizationOrganic SynthesisReaction MechanismsAmino Acid EstersC - C Coupling CatalysisC - C Coupling ReactionsCopper-catalyzed CouplingFunctional Group ToleranceLate-stage Functionalization Via Cross-couplingMild Reaction ConditionsSelectivity
The efficient copper-catalyzed cyanoalkylation of amines via C–C bond cleavage has been demonstrated. Distinctive features of this procedure involves mild conditions, broad range of nitrogen nucleophiles, high selectivity, and good functional group tolerance, thus providing a useful approach for the C(sp3)–N bond formations. Most importantly, this protocol is applicable to the late-stage functionalization of natural products, amino acid esters, and drugs. Mechanistic studies suggest that a radical intermediate was involved in this transformation.
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Amines: synthesis, properties, and applications
Choice Reviews Online · 2005 · 1.3K citations
Asymmetric copper-catalyzed C-N cross-couplings induced by visible light
Quirin M. Kainz, Carson D. Matier, Agnieszka Bartoszewicz et al. · Science · 2016 · 761 citations · Full text
Ralph Nicholas Salvatore, Cheol Hwan Yoon, Kyung Woon Jung · Tetrahedron · 2001 · 702 citations