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Dynamic Ion Speciation During Hydrolysis of Aryltrifluoroborates

preprint
submitted on 27.07.2020 and posted on 28.07.2020 by Isaac Omari, Lars Yunker, Johanne Penafiel, Darlene Gitaari, Atzin San Roman, J Scott McIndoe

Organotrifluoroborates serve as a coupling partner during transmetallation in the Suzuki-Miyaura reaction but require hydrolysis prior to the coupling reaction. Their anionic nature allows study of their hydrolysis by electrospray ionization mass spectrometry (ESI-MS) by real-time monitoring, complemented by pH analysis. Induction periods varied according to the borates employed, and a dynamic series of equilibria for numerous ions was observed during hydrolysis. We found that the induction periods and reaction rates were sensitive to the R group of the borates, the shape of reaction vessel, and stir rate, and that after complete decay of all of the aryltrifluoroborate ion the solution contained a variety of partially hydrolyzed species.

Funding

NSERC Discovery

History

Email Address of Submitting Author

mcindoe@uvic.ca

Institution

University of Victoria

Country

Canada

ORCID For Submitting Author

0000-0001-7073-5246

Declaration of Conflict of Interest

No conflict

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