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Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution

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cris.lastimport.scopus2024-02-12T20:26:38Z
dc.abstract.enElectrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C–H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorBarbasiewicz, Michał
dc.contributor.authorAntoniak, Damian
dc.date.accessioned2024-01-24T15:41:05Z
dc.date.available2024-01-24T15:41:05Z
dc.date.copyright2022-01-03
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number2
dc.description.versionFINAL_PUBLISHED
dc.description.volume24
dc.identifier.doi10.1021/ACS.ORGLETT.1C03920
dc.identifier.issn1523-7060
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/100452
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.1c03920
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofOrganic Letters
dc.relation.pages516-519
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleAlkylation of Nitropyridines via Vicarious Nucleophilic Substitution
dc.typeJournalArticle
dspace.entity.typePublication