115151-99-0Relevant academic research and scientific papers
Highly chemoselective intermolecular cross-benzoin reactions using an: Ad hoc designed novel N-heterocyclic carbene catalyst
Delany, Eoghan G.,Connon, Stephen J.
supporting information, p. 780 - 786 (2018/02/09)
The design of a novel N-heterocyclic carbene catalyst incorporating a bulky yet highly electron-deficient N-aryl substituent has allowed the development of an efficient protocol for the first highly chemoselective intermolecular benzoin condensations between two non-identical aromatic aldehydes.
A family of thiazolium salt derived N-heterocyclic carbenes (NHCs) for organocatalysis: Synthesis, investigation and application in cross-benzoin condensation
Piel, Isabel,Pawelczyk, Marius D.,Hirano, Keiichi,Froehlich, Roland,Glorius, Frank
supporting information; experimental part, p. 5475 - 5484 (2011/11/29)
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.
Reactions of Aryl Ketones and Coumarins with Iodine(III) Tris(trifluoroacetate)
Fukuyama, Norihiro,Nishino, Hiroshi,Kurosawa, Kazu
, p. 4363 - 4368 (2007/10/02)
The reaction of acetophenones with iodine(III) tris(trifluoroacetate) yields 3'- and/or 2-iodo derivatives, depending upon the substituent on the aromatic ring and the reaction conditions.The reaction was examinedby changing the molar ratio of acetophenone versus the reagent, reaction temperature, and solvent.In similar reactions flavanones and coumarins gave iodo derivatives in which iodine is incorporated at various positions orientated by the oxygen functions. 1,2-Diphenylethanone yields 2-hydroxy-2-(2-iodophenyl)-1-phenylethanone and 1-(2-iodophenyl)-2-phenylethanedione.The reactions of other aromatic ketones such as 9-xanthenone, 9-fluorenone, and anthrone also give iodo derivatives in moderate to good yields.The mechanisms for the iodination at the α-carbon to the carbonyl group have been discussed.
