Reactivity of electrogenerated N-heterocyclic carbenes in room-temperature ionic liquids.: Cyclization to 2-azetidinone ring via C-3/C-4 bond formation

被引：44

作者：

Feroci, Marta ^{[1
]}

Chiarotto, Isabella ^{[1
]}

Orsini, Monica ^{[2
]}

Sotgiu, Giovanni ^{[1
]}

Inesi, Achille ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Ingn Chim Mat Ambiente, Via Castro Laurenziano 7, I-00161 Rome, Italy

[2] Univ Roma Tre, Dipartimento Elettron Applicata, I-00146 Rome, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 09期

关键词：

carbenes; cyclization; electrochemistry; imidazolium-based RTILs; beta-lactams;

D O I：

10.1002/adsc.200800049

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：1355 / 1359

页数：5

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