Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid
Marta Feroci
DOI: 10.4236/ijoc.2011.14028   PDF    HTML     6,354 Downloads   11,183 Views   Citations


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.

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Feroci, M. (2011) Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid. International Journal of Organic Chemistry, 1, 191-201. doi: 10.4236/ijoc.2011.14028.

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The authors declare no conflicts of interest.


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