A Family of Thiazolium Salt Derived N-Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross-Benzoin Condensation

被引：135

作者：

Piel, Isabel ^{[1
]}

Pawelczyk, Marius D. ^{[1
]}

Hirano, Keiichi ^{[2
]}

Froehlich, Roland ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

[2] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 28期

关键词：

Organocatalysis; Nitrogen heterocycles; Carbenes; Umpolung; Cross-benzoin condensation; RUCL CP-ASTERISK; ETA(5)-C5ME5 MOIETY; COUPLING REACTIONS; CHIRAL THIAZOLIUM; TRIAZOLIUM SALTS; STETTER REACTION; ALDEHYDES; LIGANDS; HYDROACYLATION; CATALYSIS;

D O I：

10.1002/ejoc.201100870

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) bearing sterically demanding aryl substituents on the nitrogen and with varying backbone substitution patterns have been synthesized. Investigation of the catalytic activity of these NHCs in a number of benzoin-type coupling reactions revealed markedly different levels of reactivity and selectivity. To elucidate the underlying factors leading to differences in reactivity, a study of the electronic and steric properties of these NHC catalysts was conducted. By using the best catalyst in this study, the intermolecular cross-benzoin condensation reaction was explored in more detail.

引用

页码：5475 / 5484

页数：10

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