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Gas‐phase studies of copper catalyzed aerobic cross coupling of thiol esters and arylboronic acids |
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| Authors: | Alexandra Tsybizova Detlef Schröder Jana Roithová Adam Henke Jiři Šrogl |
| Institution: | 1. Department of Organic Chemistry, Charles University in Prague, , 12843 Prague 2, Czech Republic;2. Institute of Organic Chemistry and Biochemistry, , 166 10 Prague 6, Czech Republic;3. Department of Chemistry, Columbia University in the City of New York, , 10027 New York, USA. |
| Abstract: | 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 (ΔH?, ΔS?, and ?G?) for the title reaction. |
| Keywords: | boronic acids catalysis copper cross coupling electrospray ionization/mass spectrometry kinetic studies rate constants thiol esters thermodynamic parameters |