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Dehydrogenative coupling reactions with oxidized guanidino-functionalized aromatic compounds: novel options for σ-bond activation

We present a new option for metal-free σ-bond activation, making use of oxidized, guanidino-functionalized aromatic compounds (GFAs). We demonstrate this new option by the homocoupling reactions of thiols and phosphines. The kinetics and the reaction pathway were studied by a number of experiments (...

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Bibliographic Details
Main Authors: Wild, Ute (Author) , Federle, Stefanie (Author) , Wagner, Arne (Author) , Kaifer, Elisabeth (Author) , Himmel, Hans-Jörg (Author)
Format: Article (Journal)
Language:English
Published: 19 July 2016
In: Chemistry - a European journal
Year: 2016, Volume: 22, Issue: 34, Pages: 11971-11976
ISSN:1521-3765
DOI:10.1002/chem.201602236
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201602236
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201602236
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Author Notes:Ute Wild, Stefanie Federle, Arne Wagner, Elisabeth Kaifer, and Hans-Jörg Himmel
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Summary:We present a new option for metal-free σ-bond activation, making use of oxidized, guanidino-functionalized aromatic compounds (GFAs). We demonstrate this new option by the homocoupling reactions of thiols and phosphines. The kinetics and the reaction pathway were studied by a number of experiments (including heterocoupling of thiols and phosphines), supported by quantum-chemical computations. Reaction of the oxidized GFA with p-dihydrobenzoquinone to give p-benzoquinone shows that typical proton-coupled electron-transfer reactions are also possible.
Item Description:Gesehen am 24.08.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201602236

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