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A Family of Thiazolium Salt Derived N‐Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross‐Benzoin Condensation
Author(s) -
Piel Isabel,
Pawelczyk Marius D.,
Hirano Keiichi,
Fröhlich Roland,
Glorius Frank
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100870
Subject(s) - chemistry , steric effects , reactivity (psychology) , organocatalysis , umpolung , catalysis , benzoin , salt (chemistry) , aryl , organic chemistry , intermolecular force , condensation reaction , enantioselective synthesis , alkyl , molecule , medicine , alternative medicine , pathology , nucleophile
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.