56456-42-9Relevant articles and documents
Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio
supporting information, p. 4876 - 4894 (2021/09/20)
Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.
Fe3O4@OA-Pd and Mo10V2@NSiO2 nanoparticles: An efficient and reusable catalytic system for Heck reaction under ligand free conditions
Rafiee, Ezzat,Kahrizi, Masoud
, p. 1125 - 1138 (2016/04/26)
This paper reports the use of a novel catalytic system composed of H5PMo10V2O40 supported on nano silica (Mo10V2@NSiO2) and palladium-deposited, oleic-acid-coated Fe3O4 (Fe3O4@OA-Pd) nanoparticles, as reusable catalysts for Heck coupling reaction under ligand and base free conditions. The average particle size of catalyst was measured to be about 9 nm by transmission electron microscopy. The immobilized palladium on oleic acid coated Fe3O4 was found to be effective in the Heck arylation of various aryl bromides and especially less reactive aryl chlorides with styrene in the presence of heteropoly acid. This method has the advantages of high yields, elimination of ligand and base, simple methodology and easy workup. Interestingly, the novel catalytic system could be recovered in a facile manner from the reaction mixture and recycled several times without any significant loss in catalytic activity. Structural changes of recovered Mo10V2@NSiO2 and Fe3O4@OA-Pd were investigated before reusing for the next runs. Finally, synchronized reusability of both components of our catalytic system has been investigated in the model reaction.
Combination of palladium and oleic acid coated-magnetite particles: Characterization and using in Heck coupling reaction with magnetic recyclability
Rafiee, Ezzat,Ataei, Ali,Nadri, Shirin,Joshaghani, Mohammad,Eavani, Sara
, p. 302 - 309 (2013/12/04)
The magnetic Fe3O4 nanoparticles were prepared by co-precipitation method and coated with oleic acid. The oleic acid coated Fe3O4 (Fe@OA) particles were used for the immobilization of palladium particles to prod