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Efficient solvent-free friedel-crafts benzoylation and acylation of m-xylene catalyzed by N-acetylpyrazine-2-carbohydrazide-Fe(III)-chloro complexes

2018-07-31Journal article Restricted access
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dc.contributor.authorRoy Barman, Tannistha
dc.contributor.authorSutradhar, Manas
dc.contributor.authorAlegria, Elisabete
dc.contributor.authorGuedes Da Silva, M. Fátima C.
dc.contributor.authorKuznetsov, Maxim L.
dc.contributor.authorPombeiro, Armando
dc.date.accessioned2018-11-23T13:41:25Z
dc.date.available2018-11-23T13:41:25Z
dc.date.issued2018-07-31
dc.description.abstractReaction of N-acetylpyrazine-2-carbohydrazide (H2L) with anhydrous Fe(II) or Fe(III) chloride in CH3CN or in MeOH leads to the mononuclear [Fe(kNN’O-HL)Cl2] (1) or binuclear [Fe(kNN’O-HL) Cl(μ-OMe)]2 (2) Fe(III) complex, respectively. These complexes are characterized by elemental analysis, ESI-MS, IR spectroscopy, single-crystal X-ray crystallography, electrochemical techniques and DFT calculations. The theoretical calculations indicate that the three single-electron sequential reductions of 1 are centred at the metal, at the pyrazine group and at both, respectively. The catalytic activity of 1 and 2 was screened towards Friedel-Crafts benzoylation and acylation of m-xylene. The effects of reaction parameters, such as catalyst amount, reaction time and temperature, were studied and, under optimal conditions, 96% yield of 2,4-dimethylbenzophenone and 20% yield of 2,4-dimethylacetophenone were obtained, respectively. Complex 1 exhibited the highest activity in both reactions. The structural and electrochemical properties were supported by theoretical calculations and the importance of the Lewis acid character of the catalyst in the promotion of this catalytic reaction is discussed.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationBARMAN, Tannistha Roy; [et al] – Efficient solvent-free friedel-crafts benzoylation and acylation of m-xylene catalyzed by N-acetylpyrazine-2-carbohydrazide-Fe(III)-chloro complexes. Chemistry Select. ISSN 2365-6549. Vol. 3, N.º 28 (2018), pp. 8349-8355pt_PT
dc.identifier.doihttps://doi.org/10.1002/slct.201801656pt_PT
dc.identifier.issn2365-6549
dc.identifier.urihttp://hdl.handle.net/10400.21/9080
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWiley-VCH Verlagpt_PT
dc.relationCatalytic process tuning for Baeyer-Villiger and Henry reactions
dc.relationMETAL CLUSTERS: STRUCTURAL ANALYSIS, APPLICATIONS IN CATALYSIS AND MOLECULAR MAGNETISM
dc.subjectBenzoylationpt_PT
dc.subjectFe(III) complexespt_PT
dc.subjectFriedel-Craftspt_PT
dc.subjectReação de benzoilaçãopt_PT
dc.subjectComplexos de ferropt_PT
dc.titleEfficient solvent-free friedel-crafts benzoylation and acylation of m-xylene catalyzed by N-acetylpyrazine-2-carbohydrazide-Fe(III)-chloro complexespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCatalytic process tuning for Baeyer-Villiger and Henry reactions
oaire.awardTitleMETAL CLUSTERS: STRUCTURAL ANALYSIS, APPLICATIONS IN CATALYSIS AND MOLECULAR MAGNETISM
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FEQU-EQU%2F122025%2F2010/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00100%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F86067%2F2012/PT
oaire.citation.endPage8355pt_PT
oaire.citation.issue28pt_PT
oaire.citation.startPage8349pt_PT
oaire.citation.titleChemistrySelectpt_PT
oaire.citation.volume3pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream5876
person.familyNameRoy Barman
person.familyNameSutradhar
person.familyNameAlegria
person.familyNameGuedes da Silva
person.familyNameKuznetsov
person.familyNamePombeiro
person.givenNameTannistha
person.givenNameManas
person.givenNameElisabete
person.givenNameM. Fátima C.
person.givenNameMaxim L.
person.givenNameArmando
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person.identifier.orcid0000-0002-5147-7648
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person.identifier.orcid0000-0003-4060-1057
person.identifier.orcid0000-0003-4836-2409
person.identifier.orcid0000-0001-5729-6189
person.identifier.orcid0000-0001-8323-888X
person.identifier.ridL-7444-2014
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person.identifier.scopus-author-id36167317100
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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