10354-43-5Relevant articles and documents
Solution-phase parallel synthesis using ion-exchange resins
Suto, Mark J.,Gayo-Fung, Leah M.,Palanki, Moorthy S. S.,Sullivan, Robert
, p. 4141 - 4150 (1998)
Ion-exchange resins are useful as scavengers in solution-phase parallel synthesis. Ester and amide libraries have been generated using basic ion- exchange resins to facilitate the formation of products and to remove reaction byproducts. Acidic ion-exchang
Direct synthesis of amides from coupling of alcohols and amines catalyzed by ruthenium(II) thiocarboxamide complexes under aerobic conditions
Sindhuja, Elangovan,Ramesh, Rengan,Balaji, Sundarraman,Liu, Yu
, p. 4269 - 4278 (2014)
Four octahedral ruthenium(II) thiocarboxamide complexes of the general formula [RuClCO(AsPh3)2(L)] (L = N-substituted pyridine-2-thiocarboxamide) incorporating carbonyl and triphenylarsine have been synthesized from the reaction of 1 equiv of ruthenium precursor [RuHClCO(AsPh3)3] with 1 equiv of thiocarboxamide ligands in refluxing ethanol in the presence of base. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. Molecular structures of all the complexes were determined by X-ray crystallography, which confirm the coordination mode of thiocarboxamide and reveal the presence of a distorted octahedral geometry around the Ru ion. All the ruthenium(II) thiocarboxamide complexes were generated as highly efficient catalysts for synthesis of secondary or tertiary amides by coupling of amines and alcohols with low catalyst loading, and the maximum yield was obtained up to 97%. The coupling reaction can be readily carried out under mild aerobic conditions, and release of water is the only byproduct. Further, the effect of substituents of the ligand, solvents, reaction temperature, time, and catalyst loading on the catalytic activity of the complexes has been investigated. A plausible mechanism is proposed for the synthesis of amides via hemiaminal as intermediate through an oxidation of an alcohol to aldehyde.
Solvent-free synthesis of amides from non-enolizable esters and amines using microwave irradiation
Varma, Rajender S.,Naicker, Kannan P.
, p. 6177 - 6180 (1999)
An efficient solid state synthesis of amides is described from non- enolizable esters and amines using potassium tert-butoxide under microwave irradiation conditions.
Ion-exchange resins for solution phase parallel synthesis of chemical libraries
Gayo, Leah M.,Suto, Mark J.
, p. 513 - 516 (1997)
Described are various techniques that employ ion-exchange resins for the solution-phase synthesis of chemical libraries. We have found these resins to be useful as reagents and/or scavengers in a variety of reactions. Nine basic ion-exchange resins were e
Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
Xu-Xu, Qing-Feng,Nishii, Yuji,Uetake, Yuta,Sakurai, Hidehiro,Miura, Masahiro
supporting information, p. 17952 - 17959 (2021/11/16)
Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.
CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in waterviabenzylic sp3C-H activation
Ebrahimi, Edris,Khalafi-Nezhad, Ali,Khalili, Dariush,Rousta, Marzieh
, p. 20007 - 20020 (2021/11/12)
A magnetite-reduced graphene oxide-supported CuO nanocomposite (rGO/Fe3O4-CuO) was preparedviaa facile chemical method and characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), UV-vis spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive spectroscopy (EDS), Brunauer-Emmett-Teller (BET) analysis, vibrating-sample magnetometry (VSM), and thermogravimetric (TG) analysis. The catalytic activity of the rGO/Fe3O4-CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals usingtert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation into a single operation. Moreover, the synthesized nanocomposites can be separated from the reaction mixtures using an external magnet and reused in six consecutive runs without a noticeable decrease in the catalytic activity.
