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

  作者 PIEL ISABEL; PAWELCZYK MARIUS D; HIRANO KEIICHI; FROEHLICH ROLAND; GLORIUS FRANK  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2011年-28;  页码  5475-5484  
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[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.

 
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