Fluoride-mediated rearrangement of phenylfluorosilanes

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dc.contributor.authorDean, Natalie
dc.contributor.authorMcIndoe, J. Scott
dc.date.accessioned2018-10-10T12:44:29Z
dc.date.available2018-10-10T12:44:29Z
dc.date.copyright2018en_US
dc.date.issued2018
dc.description.abstractCombining Ph3SiF and fluoride ion under conditions used for the Hiyama coupling causes rapid formation of the expected [Ph3SiF2]−; however, real-time electrospray mass spectrometric analysis reveals that phenyl-fluoride exchange occurs concomitantly, also producing substantial quantities of [PhnSiF5–n]− (n = 0–2). The exchange process is verified using 19F NMR spectroscopy. This observation may have implications for Hiyama reaction protocols, which use transmetallation from triaryldifluorosilicates as a key step in cross-coupling.en_US
dc.description.reviewstatusRevieweden_US
dc.description.scholarlevelFacultyen_US
dc.description.sponsorshipJSM thanks NSERC (Discovery and Discovery Accelerator Supplements) for operational funding and CFI, BCKDF, and the University of Victoria for infrastructural support.en_US
dc.identifier.citationDean, N.L. & McIndoe, J.S. (2018). Fluoride-mediated rearrangement of phenylfluorosilanes. Canadian Journal of Chemistry, 96(6), 587-590. https://doi.org/10.1139/cjc-2017-0754en_US
dc.identifier.urihttps://doi.org/10.1139/cjc-2017-0754
dc.identifier.urihttp://hdl.handle.net/1828/10151
dc.language.isoenen_US
dc.publisherCanadian Journal of Chemistryen_US
dc.subjectmass spectrometry
dc.subjectelectrospray ionization
dc.subjectfluorine NMR
dc.subjectfluoride
dc.subjectsilane/silicate
dc.subjectexchange
dc.subject.departmentDepartment of Chemistry
dc.titleFluoride-mediated rearrangement of phenylfluorosilanesen_US
dc.typePostprinten_US

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