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