Gas‐phase studies of copper catalyzed aerobic  cross coupling  of thiol esters and arylboronic acids | Zendy

Tsybizova Alexandra | Zendy; Schröder Detlef | Zendy; Roithová Jana | Zendy; Henke Adam | Zendy; Šrogl Jiři | Zendy

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Gas‐phase studies of copper catalyzed aerobic cross coupling of thiol esters and arylboronic acids

Author(s) -

Tsybizova Alexandra,

Schröder Detlef,

Roithová Jana,

Henke Adam,

Šrogl Jiři

Publication year - 2014

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.3262

Subject(s) - chemistry , thiol , electrospray ionization , copper , mass spectrometry , coupling reaction , catalysis , radical , phase (matter) , ionic bonding , organic chemistry , chromatography , ion

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.

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