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Dynamic Ion Speciation during the Hydrolysis of Aryltrifluoroborates **
Author(s) -
Omari Isaac,
Yunker Lars P. E.,
Penafiel Johanne,
Gitaari Darlene,
San Roman Atzin,
McIndoe J. Scott
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004726
Subject(s) - transmetalation , hydrolysis , chemistry , electrospray ionization , mass spectrometry , electrospray , ion , boron , coupling reaction , induction period , inorganic chemistry , chromatography , organic chemistry , catalysis
Organotrifluoroborates serve as coupling partners during transmetalation 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) through real‐time monitoring, complemented by pH analysis. The induction period 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 the reaction vessel, and stir rate.