On-surface multicomponent Povarov reaction examined by paper spray mass spectrometry

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dc.creatorJoão Victor Coelho Pimenta
dc.creatorAdão Aparecido Sabino
dc.creatorRodinei Augusti
dc.date.accessioned2023-06-27T18:48:21Z
dc.date.accessioned2025-09-08T23:52:03Z
dc.date.available2023-06-27T18:48:21Z
dc.date.issued2021
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.identifier.doihttps://doi.org/10.1016/j.ijms.2021.116775
dc.identifier.issn1387-3806
dc.identifier.urihttps://hdl.handle.net/1843/55429
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofInternational Journal of Mass Spectrometry
dc.rightsAcesso Restrito
dc.subjectEspectrometria de massa
dc.subjectQuimica de superficie
dc.subjectRessonancia magnetica nuclear
dc.subjectAldeídos
dc.subjectOlefinas
dc.subjectQuímica orgânica
dc.subjectMatéria condensada
dc.subject.otherPovarov reaction
dc.subject.otherMass spectrometry
dc.subject.otherOn-surface reactions
dc.subject.otherPaper spray ionization
dc.titleOn-surface multicomponent Povarov reaction examined by paper spray mass spectrometry
dc.typeArtigo de periódico
local.citation.spage116775
local.citation.volume472
local.description.resumoPovarov multicomponent reaction (MCR) is an acid-catalyzed process that uses three distinct classes of reactants. i. e. an aldehyde, aniline, and activated alkene. We employ paper spray ionization mass spectrometry (PS-MS) as a convenient platform for investigating the on-surface Povarov reaction using the following suitable prototype starting reactants: the tag-charged aldehyde 1, 4-bromoaniline, 2,3-dihydrofuran, and formic acid. The PS(þ)-MS revealed, besides the formation of the Povarov product (a tetrahydroquinoline compound), the transitional imine. Moreover, the oxonium intermediate was also detected as the water and formic acid adducts. Other alkenes (2,3-dihydropyran and styrene), acid catalysts (acetic acid and p-sulfonic acid calix[4]arene), and aldehydes (4-nitrobenzaldehyde, 4-anisaldehyde, 4-methoxycinnamaldehyde, citronellal, and valeraldehyde) were employed to verify the reaction generality. We observed that styrene (an unactivated alkene), p-sulfonic acid calix [4] arene (an acid with a non-nucleophilic conjugated base), and aromatic aldehydes (4-nitrobenzaldehyde and 4-anisaldehyde) showed lower reactivity than the other reactants. In conclusion, an exciting possibility emerges as PS-MS can be widely employed to investigate similar on-surface organic reactions to verify the connections between the on-surface and condensed phase processes.
local.identifier.orcidhttps://orcid.org/0009-0008-2944-5536
local.identifier.orcidhttps://orcid.org/0000-0003-1265-7694
local.identifier.orcidhttps://orcid.org/0000-0002-9448-9518
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S1387380621002566

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