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Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates

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dc.abstract.enStudies on directed ortho-metalation (DoM) of arenesulfonyl fluorides (ArSO2F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, –78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO2F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO2F) display fragmentation to arynes and migration of the SO2F group to the ortho position (anionic thia-Fries rearrangement).
dc.affiliationUniwersytet Warszawski
dc.contributor.authorAntoniak, Damian
dc.contributor.authorBarbasiewicz, Michał
dc.contributor.authorTalko, Alicja
dc.date.accessioned2024-01-24T21:49:48Z
dc.date.available2024-01-24T21:49:48Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.number11
dc.description.volume51
dc.identifier.doi10.1055/S-0037-1610877
dc.identifier.issn0039-7881
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/104924
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofSynthesis
dc.relation.pages2278-2286
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.ensulfonyl fluorides
dc.subject.enfluorosulfates
dc.subject.endirected ortho-metalation
dc.subject.enSuFEx
dc.subject.enorthogonal reactivity
dc.subject.enin situ trap
dc.subject.enlithium amides
dc.subject.enanionic thia-Fries rearrangement
dc.titleDirected ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates
dc.typeJournalArticle
dspace.entity.typePublication