Synthetic and Mechanistic Studies on Pd(0)-Catalyzed Diamination of Conjugated Dienes

• Published in: Journal of the American Chemical Society Vol. 132; no. 10; pp. 3523 - 3532
• Main Authors: Zhao, Baoguo, Du, Haifeng, Cui, Sunliang, Shi, Yian
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 17.03.2010
• Subjects: Alkadienes - chemistry; Amination; Aziridines - chemistry; Catalysis; Diamines - chemical synthesis; Kinetics; Magnetic Resonance Spectroscopy - methods; Organophosphorus Compounds - chemistry; Palladium - chemistry

Various dienes and a triene can be regioselectively diaminated at the internal double bond with good yields and high diastereoselectivity using di-tert-butyldiaziridinone (5) as the nitrogen source and Pd(PPh3)4 (1−10 mol %) as the catalyst. Kinetic studies with 1H NMR spectroscopy show that the dia...