{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Shen K"],"funding":["Division of Chemistry","Camille and Henry Dreyfus Foundation","Alfred P. Sloan Foundation","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["13110-13116"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5685496"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["139(37)"],"pubmed_abstract":["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, on"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles."],"pmcid":["PMC5685496"],"funding_grant_id":["R01 GM118786","CHE-1455220","GM118786"],"pubmed_authors":["Shen K","Wang Q"],"additional_accession":[]},"is_claimable":false,"name":"Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.","description":"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, on","dates":{"release":"2017-01-01T00:00:00Z","publication":"2017 Sep","modification":"2025-04-22T21:13:53.931Z","creation":"2019-03-26T23:56:26Z"},"accession":"S-EPMC5685496","cross_references":{"pubmed":["28825822"],"doi":["10.1021/jacs.7b06852"]}}