Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202004726
Keywords
aryltrifluoroborates; hydrolysis; ion speciation; pH analysis; real-time monitoring
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Funding
- NSERC
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Organotrifluoroborates are used as coupling partners in the Suzuki-Miyaura reaction, but require hydrolysis before the coupling reaction. Electrospray ionization mass spectrometry (ESI-MS) allows real-time monitoring of their hydrolysis, complemented by pH analysis. The induction periods and reaction rates during hydrolysis were found to be sensitive to the R group of the borates, the shape of the reaction vessel, and stir rate.
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.
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