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

Zhongyi Zeng, Hongming Jin, Jin Xie, Bing Tian, Matthias Rudolph, Frank Rominger and A. Stephen K. Hashmi*

*Organisch-Chemisches Institut, Ruprecht-Karls-Universitšt Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: hashmihashmi.de

Z. Zeng, H. Jin, J. Xie, B. Tian, M. Rudolph, F. Rominger, A. S. K. Hashmi, Org. Lett., 2017, 19, 1020-1023.

DOI: 10.1021/acs.orglett.7b00001 (free Supporting Information)



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Abstract

A gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides enables an atom-economical synthesis of fully substituted 4-aminoimidazoles. The reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.

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Key Words

imidazoles


ID: J54-Y2017