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      Acilação de Friedel-Crafts do 2-metoxinaftaleno usando o ácido dodecafosfotúngstico suportado em sílica (HPW/SiO2) como catalisador e acetonitrila como solvente Translated title: Friedel-Crafts acylation of the 2-methoxynaphthalene using the silica-supported dodecatungstophosphoric acid (HPW/SiO2) as catalyst and acetonitrile as solvent

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          Translated abstract

          The synthesis of fine chemicals intermediates using Friedel-Crafts acylation is one of the most important methods in chemical technology. In this work, the acylation of 2-methoxynaphthalene with acetic anhydride using a silica-supported dodecatungstophosphoric acid catalyst (HPW/SiO2) and acetonitrila as solvent was studied, showing that this reaction is a feasible alternative to produce intermediaries to replace the current methods of production. The reactions using acetonitrile solvent showed yields greater than or equal to the reactions using traditional solvents such as nitrobenzene and dichloroethane. Finally, the modified Eley-Rideal mechanism was proposed to elucidate the experimental data obtained.

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          Most cited references 44

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          Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C–H Functionalization Sequences

          A Rh-catalyzed C–H bond activation/alkenylation/electrocyclization cascade reaction provides diverse 1,2-dihydropyridines from simple and readily available precursors. The reaction can be carried out at low (<1%) Rh-catalyst loadings, and the use of the robust, air-stable Rh precatalyst, [RhCl(cod)]2, enables the cascade reaction to be easily performed on the benchtop. The 1,2-dihydropyridine products serve as extremely versatile synthetic intermediates for further elaboration often without isolation. The addition of electrophiles under kinetic or thermodynamic conditions provides a wide range of iminiums. Subsequent addition of a nucleophile then generates a diverse array of differently substituted piperidine products. Additionally, [3 + 2] and [4 + 2] cycloadditions of the 1,2-dihydropyridine intermediate provides access to bridged bicyclic structures such as tropanes and isoquinuclidines. These concise reaction sequences enable the formation of highly substituted piperidines in synthetically useful yields with excellent diastereoselectivity.
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              The Friedel-Crafts Acylation Reaction and its Application to Polycyclic Aromatic Hydrocarbons

               P. H. Gore (1955)
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                Author and article information

                Affiliations
                [1 ] Universidade Estadual do Sudoeste da Bahia Brazil
                Contributors
                Role: ND
                Role: ND
                Role: ND
                Journal
                qn
                Química Nova
                Quím. Nova
                Sociedade Brasileira de Química (São Paulo )
                1678-7064
                2010
                : 33
                : 1
                : 57-64
                S0100-40422010000100012
                10.1590/S0100-40422010000100012

                http://creativecommons.org/licenses/by/4.0/

                Product
                Product Information: SciELO Brazil
                Categories
                CHEMISTRY, MULTIDISCIPLINARY

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