biostudies-literatureShen KDivision of ChemistryCamille and Henry Dreyfus FoundationAlfred P. Sloan FoundationNational Institute of General Medical SciencesNIGMS NIH HHS13110-13116https://www.ebi.ac.uk/biostudies/studies/S-EPMC5685496biostudies-literatureUnknown139(37)A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precursors onto both terminal and internal alkenes, with remarkable regio- and stereoselectivity. Mechanistic studies show that this diamination reaction proceeds via a nucleophilic amino cyclization followed by an intermolecular C-N bond formation using electrophilic azidoiodinane. This pathway differs from previous azidoiodinane-initiated alkene functionalization, suggesting new reactivity of azidoiodinane. Furthermore, this aminoazidation reaction provides an efficient strategy to introduce azide, one of the most useful chemical reporters, onJournal of the American Chemical SocietyCopper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.PMC5685496R01 GM118786CHE-1455220GM118786Shen KWang QfalseCopper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precursors onto both terminal and internal alkenes, with remarkable regio- and stereoselectivity. Mechanistic studies show that this diamination reaction proceeds via a nucleophilic amino cyclization followed by an intermolecular C-N bond formation using electrophilic azidoiodinane. This pathway differs from previous azidoiodinane-initiated alkene functionalization, suggesting new reactivity of azidoiodinane. Furthermore, this aminoazidation reaction provides an efficient strategy to introduce azide, one of the most useful chemical reporters, on2017-01-01T00:00:00Z2017 Sep2025-04-22T21:13:53.931Z2019-03-26T23:56:26ZS-EPMC56854962882582210.1021/jacs.7b06852