Unveiling the mechanism of N-methylation of indole with dimethylcarbonate using either DABCO or DBU as catalyst

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dc.contributor.authorVendramini P.H.
dc.contributor.authorZeoly L.A.
dc.contributor.authorCormanich R.A.
dc.contributor.authorBuehl M.
dc.contributor.authorEberlin M.N.
dc.contributor.authorFerreira B.R.V.
dc.date.accessioned2024-03-12T19:21:09Z
dc.date.available2024-03-12T19:21:09Z
dc.date.issued2021
dc.description.abstract© 2021 John Wiley & Sons, Ltd.Depending on the catalyst used, N-methylation of indole with dimethylcarbonate (DMC)—an environmentally friendly alkylation agent—yields different products. With 1,4-diazabicyclo[2.2.2]octane (DABCO), the reaction forms only N-methylated indole, but with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), both N-methylated and N-methoxycarbonylated indole are formed. Using direct ESI(+)-MS monitoring to collect actual snapshots of the changing ionic composition of the reaction solution, we report on the interception and characterization of key intermediates for such reactions. Although a mechanism has been proposed with methoxycarbonylated base as the key intermediate for both DBU and DABCO, the ESI(+)-MS data and B3LYP-D3/6-311+G** calculations suggest that the reaction of DMC with indole under either DABCO or DBU catalysis follows contrasting mechanisms.
dc.description.issuenumber3
dc.description.volume56
dc.identifier.doi10.1002/jms.4707
dc.identifier.issn1096-9888
dc.identifier.urihttps://dspace.mackenzie.br/handle/10899/34695
dc.relation.ispartofJournal of Mass Spectrometry
dc.rightsAcesso Restrito
dc.subject.otherlanguagedensity functional theory calculations
dc.subject.otherlanguageESI(+)-MS/MS
dc.subject.otherlanguageindole
dc.subject.otherlanguagemechanism
dc.subject.otherlanguageN-methylation
dc.titleUnveiling the mechanism of N-methylation of indole with dimethylcarbonate using either DABCO or DBU as catalyst
dc.typeArtigo
local.scopus.citations4
local.scopus.eid2-s2.0-85101465873
local.scopus.subject1 ,4-diazabicyclo[2.2.2]octane
local.scopus.subject1 ,8-diazabicyclo[5.4.0]undec-7-ene
local.scopus.subjectDimethyl carbonate
local.scopus.subjectIonic composition
local.scopus.subjectN-methylation
local.scopus.subjectReaction solutions
local.scopus.updated2024-12-01
local.scopus.urlhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85101465873&origin=inward
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