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Reactivity of Electrogenerated N‐Heterocyclic Carbenes in Room‐Temperature Ionic Liquids. Cyclization to 2‐Azetidinone Ring via C‐3/C‐4 Bond Formation
Author(s) -
Feroci Marta,
Chiarotto Isabella,
Orsini Monica,
Sotgiu Giovanni,
Inesi Achille
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800049
Subject(s) - chemistry , electrosynthesis , ionic liquid , ring (chemistry) , reactivity (psychology) , hydrogen bond , electrolysis , ionic bonding , electrochemistry , medicinal chemistry , bond cleavage , combinatorial chemistry , inorganic chemistry , photochemistry , organic chemistry , catalysis , ion , molecule , electrode , electrolyte , medicine , alternative medicine , pathology
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/C4 bond formation. The electrosynthesis of β‐lactams 2a–k has been achieved under mild conditions, elevated yields and avoiding the use of toxic, volatile, molecular solvents.