On-surface multicomponent Povarov reaction examined by paper spray mass spectrometry
Carregando...
Data
Título da Revista
ISSN da Revista
Título de Volume
Editor
Universidade Federal de Minas Gerais
Descrição
Tipo
Artigo de periódico
Título alternativo
Primeiro orientador
Membros da banca
Resumo
Povarov 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.
Abstract
Assunto
Espectrometria de massa, Quimica de superficie, Ressonancia magnetica nuclear, Aldeídos, Olefinas, Química orgânica, Matéria condensada
Palavras-chave
Povarov reaction, Mass spectrometry, On-surface reactions, Paper spray ionization
Citação
Departamento
Curso
Endereço externo
https://www.sciencedirect.com/science/article/pii/S1387380621002566