期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 37, 页码 13110-13116出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06852
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资金
- Duke University
- National Institute of General Medical Sciences of the NIH [GM118786]
- National Science Foundation [CHE-1455220]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1455220] Funding Source: National Science Foundation
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, onto a broad range of bioactive azaheterocycles, offering new opportunities in bioorthogonal chemistry and biological studies. Rapid syntheses of 5-HT2C agonist, (-)-enduracididine and azido-cholesterol derivatives demonstrate broad applications of this method in organic synthesis, medicinal chemistry, and chemical biology.
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