14683-47-7Relevant articles and documents
On the Virtue of Indium in Reduction Reactions. A Comparison of Reductions Mediated by Indium and Zinc: Is Indium Metal an Effective Catalyst for Zinc Induced Reductions?
Matassini, Camilla,Bonanni, Marco,Marradi, Marco,Cicchi, Stefano,Goti, Andrea
supporting information, p. 1106 - 1113 (2019/12/24)
Indium(0)-mediated reductions have been reported for the transformation of several functional groups (imines, oximes, nitro groups, isoxazolidines, and conjugated alkenes, among others), prompted by the opportunity of performing the reactions in aqueous media and green conditions. We describe here the comparison of several reactions using indium or the less expensive zinc, carried out in order to evaluate the effective advantages brought about indium metal. We found some reactions for which use of In is mandatory and others where Zn worked equally well or even better. The reduction of hydroxylamines to the corresponding amines was the only reduction for which use of In provided much better results than Zn and was also possible to apply an efficient catalytic version with use of 2–5 mol-% In in the presence of stoichiometric Zn. Applicability of this catalytic reduction to “one-pot” model processes is also demonstrated.
Methyl fluoroalkanoate as methyl-transferring reagent. Unexpected participation of BAl2 (SN2) mechanism in the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with amines
Dolensky, Bohumil,Kví?ala, Jaroslav,Paleta, Old?ich
, p. 31 - 35 (2016/04/05)
In the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with arylamines or arylmethylamines, an unexpected methyl transfer from the ester to the amine by the BAl2 (SN2) mechanism was observed leading to the corresponding N-methylamines under specific conditions. The reaction was accompanied by the formation of amides via BAc2 mechanism. The unexpected methyl transfer is highly dependent on the structure of the starting amine and is supported by the absence of solvent and high temperature.
Methanol dehydrogenation by iridium N-heterocyclic carbene complexes
Campos, Jesús,Sharninghausen, Liam S.,Manas, Michael G.,Crabtree, Robert H.
, p. 5079 - 5084 (2015/06/16)
A series of homogeneous iridium bis(N-heterocyclic carbene) catalysts are active for three transformations involving dehydrogenative methanol activation: acceptorless dehydrogenation, transfer hydrogenation, and amine monoalkylation. The acceptorless dehydrogenation reaction requires base, yielding formate and carbonate, as well as 2-3 equivalents of H2. Of the few homogeneous systems known for this reaction, our catalysts tolerate air and employ simple ligands. Transfer hydrogenation of ketones and imines from methanol is also possible. Finally, N-monomethylation of anilines occurs through a borrowing hydrogen reaction. Notably, this reaction is highly selective for the monomethylated product.