Experimental Investigation of an Oxidative C−C Coupling Reaction Catalyzed by HAuCl4

Reaction monitoring by electrospray (ESI) mass spectrometry (MS) is a valuable technique to investigate reaction mechanisms. It allows a glimpse into the reacting solution and the characterization of transient intermediates by tandem mass spectrometry. Herein we studied an intriguing gold(III)‐catal...

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Bibliographic Details
Published in:Israel journal of chemistry 2023-08, Vol.63 (7-8), p.n/a
Main Authors: Krause, Melanie T. S., Schuppener, Kim, Wegner, Hermann A., Engeser, Marianne
Format: Article
Language:English
Subjects:
Chemical reactions
Chemical synthesis
electrospray
gold
Mass spectrometry
massspectrometry
oxidative coupling
Reaction intermediates
reaction mechanism
Reaction mechanisms
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Summary:Reaction monitoring by electrospray (ESI) mass spectrometry (MS) is a valuable technique to investigate reaction mechanisms. It allows a glimpse into the reacting solution and the characterization of transient intermediates by tandem mass spectrometry. Herein we studied an intriguing gold(III)‐catalyzed synthesis of dicoumarins which includes a combination of hydroarylation and homocoupling steps. Reactants and products could be detected in positive mode. In negative mode, some species corroborating proposed transient intermediates could be detected by direct infusion ESI of reacting solutions. The ions were characterized by accurate mass determinations and gas‐phase fragmentation. Thus, indications for the nature and ligand sphere of reaction intermediates in the catalytic cycle could be collected. Supporting Information (Additional ESI spectra, CID spectra, and temporal evolution charts from reaction monitoring) for this article is available on the WWW.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.202300071