The intrinsic chemistry of imidazolium-based room-temperature ionic liquids, related to the acidity of the C-2 imidazolium cation, can be modified via cathodic cleavage of the C-2/hydrogen bond. N-Heterocyclic carbenes, electrogenerated by electrolysis of imidazolium-based room-temperature ionic liquids, are stable bases that are strong enough to deprotonate bromoamides 1a-k yielding the azetidin-2-one ring via C-3/C-4 bond formation. The electrosynthesis of beta-lactams 2a-k has been achieved under mild conditions, elevated yields and avoiding the use of toxic, volatile, molecular solvents.
Feroci, M., Chiarotto, I., Orsini, M., Sotgiu, G., Inesi, A. (2008). Reactivity of electrogenerated N-heterocyclic carbenes in room-temperature ionic liquids. Cyclization to 2-azetidinone ring via C-3/C-4 bond formation. ADVANCED SYNTHESIS & CATALYSIS, 350, 1355-1359.
Reactivity of electrogenerated N-heterocyclic carbenes in room-temperature ionic liquids. Cyclization to 2-azetidinone ring via C-3/C-4 bond formation
ORSINI, MONICA;SOTGIU, Giovanni;
2008-01-01
Abstract
The intrinsic chemistry of imidazolium-based room-temperature ionic liquids, related to the acidity of the C-2 imidazolium cation, can be modified via cathodic cleavage of the C-2/hydrogen bond. N-Heterocyclic carbenes, electrogenerated by electrolysis of imidazolium-based room-temperature ionic liquids, are stable bases that are strong enough to deprotonate bromoamides 1a-k yielding the azetidin-2-one ring via C-3/C-4 bond formation. The electrosynthesis of beta-lactams 2a-k has been achieved under mild conditions, elevated yields and avoiding the use of toxic, volatile, molecular solvents.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
