58008-11-0Relevant academic research and scientific papers
N-alkylation of amines with alcohols catalyzed by a water-soluble cp*iridium complex: An efficient method for the synthesis of amines in aqueous media
Kawahara, Ryoko,Fujita, Ken-Ichi,Yamaguchi, Ryohei
supporting information; experimental part, p. 1161 - 1168 (2011/06/24)
An efficient and environmentally benign catalytic system for the synthesis of various organic amines catalyzed by the water-soluble and air-stable (pentamethylcyclopentadienyl)-iridium-ammine iod- ide complex, [Cp*Ir(NH3)3][I]2 (Cp= pentamethylcyclopentadienyl), has been developed. A wide variety of secondary and tertiary amines were synthesized by the N-alkylation reactions of theoretical equivalents of amines with alcohols in water under air without a base. The synthesis of cyclic amines was also achieved by the N-alkylation of benzylamine with diols. Furthermore, the recycle use of the present water-soluble Cp*Ir catalyst was accomplished. Copyright
Alcohols for the α-alkylation of methyl ketones and indirect aza-wittig reaction promoted by nickel nanoparticles
Alonso, Francisco,Riente, Paola,Yus, Miguel
experimental part, p. 4908 - 4914 (2009/05/27)
Nickel nanoparticles have been found to activate primary alcohols used for the α-alkylation of ketones or in indirect aza-Wittig reactions. These processes involve hydrogen transfer from the alcohol to the intermediate α,β-unsaturated ketone or imine, respectively. All these reactions are carried out in the absence of any ligand, hydrogen acceptor or base under mild reaction conditions. For the first time nickel is employed as a potential alternative to noble-metal-based catalysts in both reactions. A reaction mechanism is proposed on the basis of some deuteration experiments. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
NADH MODELS-19 CYCLOPROPANE RING AS A CHEMICAL PROBE IN THE STUDY OF THE MECHANISM OF HYDROGEN TRANSFER BY 1,4-DIHYDROPYRIDINE DERIVATIVES
Meijer, Louis H. P.,van Niel, Johannes C. G.,Pandit, Upendra K.
, p. 5185 - 5196 (2007/10/02)
N-(Cyclopropylmethylene)phenylamines (1a-c), cyclopropyl 2-pyridyl ketones (5a-c) and ethyl cyclopropylmethylenepyruvate (14) have been subjected to reduction by 1,4-dihydropyridines in the presence of magnesium ions, and by tin hydrides.The reactions with 1,4-dihydropyridines do not involve cleavage of the three-membered ring in the reduction step.The observed acyclic product from 2-pyridyl 2,2-dimethylcyclopropyl ketone (5b) is a consequence of ring cleavage prior to reduction of the carbonyl function.In contrast, reduction of 1a-c and 5a-c by tin hydrides leads to products in which the cyclopropane moiety has undergone ring-opening.These findings support a hydride transfer mechanism for reductions with NADH models.
