4.8 Article

α-Imino Gold Carbenes from 1,2,4-Oxadiazoles: Atom-Economical Access to Fully Substituted 4-Aminoimidazoles

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ORGANIC LETTERS
卷 19, 期 5, 页码 1020-1023

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00001

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  1. Guangzhou Elite Scholarship Council
  2. CSC (China Scholarship Council)

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A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access a-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.

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