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.