Metal-Free Iodine/TEMPO-Mediated Aerobic Oxidative Ugi-Type Multicomponent Reactions with Tertiary Amines
Dengke Li1, Xianfu Shen1, Jian Lei2
1College of Chemistry and Environmental Science; Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control , Qujing Normal University , Qujing 655011 , Yunnan , China.
Abstract:
A novel aerobic oxidative Ugi-type multicomponent reaction (MCR) with tertiary amines was developed. The reaction was initiated by C(sp3)-H oxidation of the amine, followed by nucleophilic attack on the highly reactive isocyanide, generating nitrilium ion intermediates. If these intermediates were trapped by water in the system, α-amido amines could be delivered as the Ugi-3CR products. If exogenous TMSN3 was added, α-tetrazolo amines could be furnished as the first example of oxidative Ugi-azide MCR products.
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