Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 27, Issue 3, Pages 198-203Publisher
WILEY-BLACKWELL
DOI: 10.1002/poc.3262
Keywords
boronic acids; catalysis; copper; cross coupling; electrospray ionization; mass spectrometry; kinetic studies; rate constants; thiol esters; thermodynamic parameters
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Funding
- Academy of Sciences of the Czech Republic [RVO 61388963]
- European Research Council (AdG HORIZOMS)
- Grant Agency of the Czech Republic [207/11/0338 a 207/12/0846]
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Electrospray ionization/mass spectrometry (ESI-MS) is used to monitor a Cu-catalyzed aerobic cross-coupling reaction between thiol esters and arylboronic acids. The ESI spectra show the formation of Cu-complexes with the starting thiol ester 1 and the coupling product. The formation of an ionic complex at m/z 305 is observed, most likely occurring upon the elimination of a mixed anhydride from [(1)CuOAc](+). An online monitoring of the reaction using ESI-MS was carried out allowing calculation of rate constants and thermodynamic parameters (H-double dagger, S-double dagger, and G(double dagger)) for the title reaction.
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