Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/6140
DC FieldValueLanguage
dc.contributor.authorPizzetti, Mariannaen_us
dc.contributor.authorDe Luca, E.en_us
dc.contributor.authorPetricci, Elenaen_us
dc.contributor.authorPorcheddu, A.en_us
dc.contributor.authorTaddei, Maurizioen_us
dc.date.accessioned2021-03-30T15:59:56Z-
dc.date.available2021-03-30T15:59:56Z-
dc.date.issued2012-
dc.identifier.issn1615-4150en_US
dc.identifier.urihttp://hdl.handle.net/20.500.12779/6140-
dc.description54567en_US
dc.description.abstractThe synthesis of benzimidazoles starting from o-phenylenediamines and amines in the presence of palladium on charcoal as catalyst is reported. Under microwave dielectric heating it is possible to use a tertiary, a secondary, and even a primary amine as the substrate for a palladium mediated process to get 2-substituted or 1,2-disubstituted benzimidazoles, depending on the nature of the o-phenylendiamine employed. Primary amines are the most suitable reagents for the atom economy of the overall process that resulted to be general as several different substituted benzimidazoles were obtained in good yield. Benzoxazoles can be also prepared starting from primary amines and o-aminophenol. The reaction is also highly selective as no (poly)-alkylated phenylendiamines or cross-contaminated benzimidazoles are obtained starting from N-monoalkylphenylen-diamines. This behavior was interpreted as a scarce aptitude to dehydrogenation of the methylene bonded to the aromatic NH of N-alkyl-arylamines. The experiments carried out consent to draw an almost complete picture of the reaction pathways occurring during the process. The catalyst can be recycled several times and, although far from optimal performances, catalyst TON = 90 is encouraging for further large scale optimization protocols. In addition, palladium on charcoal catalyzed microwave assisted reaction of o-phenylendiamine gives tertiary amines de-alkylation and transformation into the secondary onesen_US
dc.language.isoenen_US
dc.relationNoneen_US
dc.relation.ispartofADVANCED SYNTHESIS & CATALYSISen_US
dc.titleA general approach to substituted benzimidazoles and benzoxazoles via heterogeneous palladium catalyzed hydrogen transfer with primary aminesen_US
dc.typeArticleen_US
dc.identifier.scopus2-s2.0-84865704782en_US
dc.identifier.isiWOS:000308329300017en_US
dc.relation.volume354en_US
dc.description.firstpage2453en_US
dc.description.lastpage2464en_US
dc.description.thirdmissionNot applicableen_US
item.cerifentitytypePublications-
item.grantfulltextnone-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypeArticle-
item.fulltextNo Fulltext-
crisitem.author.orcid0000-0002-9685-6342-
crisitem.author.orcid0000-0001-8660-7580-
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