Copper-Catalyzed Cascade Cyclization Reactions of Isocyanides with α-Diazocarbonyls as N-Terminal Electrophiles: Efficient Synthesis of 2-Imidazolines and 1,1′-Biimidazoles

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• 作者：Xiu-Bin Bu ; Yang Yu ; Bin Li ; Lu Zhang ; Jia-Jia Chen and Yu-Long Zhao
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2017
• 出版时间：January 19, 2017
• 年：2017
• 卷：359
• 期：2
• 页码：351-356
• 全文大小：1422K
• ISSN：1615-4169

文摘

The reactions of α-diazocarbonyls have been extensively studied and widely applied in organic synthesis acting as 1,3-dipoles, metal carbene precursors and C-nucleophiles. However, the utility of the electrophilic capability of their terminal nitrogen has been a challenging problem. Herein, a novel copper-catalyzed cascade cyclization reaction of isocyanides with α-diazocarbonyls as N-terminal electrophiles has been developed for the first time. The reaction involves a sequential intermolecular nucleophilic addition/[3+2] cycloaddition/intramolecular cyclization-ring-opening/elimination procedure and provides a new and efficient method for the construction of imidazolines and biimidazoles in a single step from readily available starting materials under very mild conditions.