Fluoride-mediated rearrangement of phenylfluorosilanes

Date

2018

Authors

Dean, Natalie
McIndoe, J. Scott

Journal Title

Journal ISSN

Volume Title

Publisher

Canadian Journal of Chemistry

Abstract

Combining 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.

Description

Keywords

mass spectrometry, electrospray ionization, fluorine NMR, fluoride, silane/silicate, exchange

Citation

Dean, 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-2017-0754