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S. Simonovic, J.-C. Frison, H. Koyuncu, A. C. Whitwood and R. E. Douthwaite, “Addition of N-Heterocyclic Car- benes to Imines: Phenoxide Assisted Deprotonation of an Imidazolium Moiety and Generation of Breslow Inter- mediates Derived from Imines,” Organic Letters, Vol. 11, No. 1, 2009, pp. 245-247. doi:10.1021/ol802572n

has been cited by the following article:

• TITLE: Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid

  AUTHORS: Marta Feroci

  KEYWORDS: Electrosynthesis, NHC, Staudinger Synthesis, ?-Lactams, Organocatalyst, Ionic Liquid

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.1 No.4, December 27, 2011

  ABSTRACT: Electrogenerated N-heterocyclic carbene (NHC), obtained by cathodic reduction of Bmim-BF4, behaves as organocatalyst and base in the Staudinger synthesis from an acyl chloride and a deactivated imine in ionic liquid to yield ?-lactams. The effect of many parameters (temperature, amount of electricity, substituents, presence of an external base) has been evaluated and a tentative mechanism for the Staudinger synthesis in a very polar medium like the ionic liquid reported. The yields of isolated ?-lactams are good, starting from non-electrophilic imines, and predominantly trans lactams are obtained with a good diastereomeric ratio.