Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species

• Published in: Journal of the American Chemical Society Vol. 133; no. 51; pp. 20890 - 20900
• Main Authors: Zhao, Baoguo, Peng, Xingao, Zhu, Yingguang, Ramirez, Thomas A, Cornwall, Richard G, Shi, Yian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.12.2011; Amer Chemical Soc
• Subjects: Amination; Aziridines - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Copper - chemistry; Physical Sciences; Polyenes - chemistry; Science & Technology; Stereoisomerism; AZIDE-ALKYNE CYCLOADDITION; PD-CATALYZED DIAMINATION; PROMOTED INTRAMOLECULAR DIAMINATION; ELECTROPHILIC DIAMINATION; ASYMMETRIC DIAMINATION; FREE-RADICAL REACTIONS; TERMINAL OLEFINS; PALLADIUM-CATALYZED DIAMINATION; C-H ACTIVATION; VICINAL DIAMINATION

Conjugated dienes can be diaminated at the internal and/or terminal double bonds using Cu(I) as catalyst and N,N-di-t-butyldiaziridinone (1) as nitrogen source. The regioselectivity is highly dependent upon the choice of Cu(I) catalyst and the substituents on diene substrates. The diamination likely...