Gas-phase study on the C-C coupling of naphthol catalyzed by Cu IITMEDA: evidence for the key role of binuclear clusters

Chemistry : a European Journal
Jana Roithová, Detlef Schröder

Abstract

The mechanism of oxidative coupling of two naphthol molecules to form binaphthol catalyzed by Cu(OH)ClTMEDA (TMEDA=N,N,N',N'-tetramethylethylenediamine) was approached by means of a gas-phase model system. Concise evidence is provided that the coupling reaction proceeds in clusters with two Cu(II) centers, whereby the intermediacy of free naphthoxy radicals in the coupling step is avoided. In the absence of TMEDA, the cluster is bound via a bridging counterion and the coupling reaction is followed by cluster cleavage. The coordination of one or two TMEDA molecules to the reactive complex results in more efficient coupling of naphthol molecules, and moreover, the binuclear cluster is also conserved after the reaction is completed. The effect of TMEDA is twofold: First, it supports clustering of copper and, second, as a ligand bound to a copper center in the reactive complex, it weakens the bond between copper and the naphtholato ligand such that the naphtholato unit is more prone to undergo C--C coupling. Furthermore, a pronounced counterion effect is found that correlates well with condensed-phase data: weakly bridging counterions (e.g., NO3(-)) yield less stable dicopper clusters and the coupling reaction hardly occurs, wherea...Continue Reading

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Citations

Dec 8, 2007·Journal of the American Society for Mass Spectrometry·Sophie RochutHelmut Schwarz
May 4, 2010·Journal of the American Society for Mass Spectrometry·Jing ZhouYinlong Guo
May 22, 2008·Chemistry : a European Journal·Francesca R NovaraHelmut Schwarz
Apr 1, 2011·Rapid Communications in Mass Spectrometry : RCM·Jana Jaklová DytrtováMichael Komárek
Oct 22, 2010·Journal of Mass Spectrometry : JMS·Agnes RévészJana Roithová
May 9, 2012·Chemistry : a European Journal·Francisco Juliá-HernándezJosé Vicente
Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl
Aug 12, 2015·Chemistry : a European Journal·Xiaobo XieZongxiu Nie
May 16, 2015·Mass Spectrometry Reviews·Alexandra Tsybizova, Jana Roithová
Jun 9, 2009·Chemical Communications : Chem Comm·Jiri SroglDetlef Schröder
Jul 28, 2011·Chemical Society Reviews·Jana Roithová
Jul 23, 2009·Chemical Society Reviews·Gerard P McGlacken, Lorraine M Bateman
Dec 4, 2009·Journal of the American Chemical Society·Jana Roithová, Petr Milko
Mar 17, 2009·The Journal of Organic Chemistry·Giovanni W AmaranteFernando Coelho
Feb 18, 2012·Journal of the American Chemical Society·Esther BoessMartin Klussmann
Mar 14, 2008·The Journal of Physical Chemistry. B·Nikos G TsierkezosHelmut Schwarz

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