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Connecting organic redox-active building blocks through mild noncatalytic C−H activation

Compounds with two or more redox-active units, connected by a bridge that supports electronic coupling between the units, have been studied for a long time. Redox reactions could result in mixed-valence compounds, in which the electronic structure depends on the degree of electronic coupling. Here w...

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Bibliographic Details
Main Authors: Wild, Ute (Author) , Hübner, Olaf (Author) , Enders, Markus (Author) , Kaifer, Elisabeth (Author) , Himmel, Hans-Jörg (Author)
Format: Article (Journal)
Language:English
Published: 01 April 2022
In: European journal of organic chemistry
Year: 2022, Issue: 15, Pages: 1-18
ISSN:1099-0690
DOI:10.1002/ejoc.202200349
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/ejoc.202200349
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202200349
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Author Notes:Ute Wild, Olaf Hübner, Markus Enders, Elisabeth Kaifer, and Hans-Jörg Himmel
Description
Summary:Compounds with two or more redox-active units, connected by a bridge that supports electronic coupling between the units, have been studied for a long time. Redox reactions could result in mixed-valence compounds, in which the electronic structure depends on the degree of electronic coupling. Here we report the synthesis of the first molecule in which two redox-active guanidines are connected through a bridge. The compound is synthesized in an unprecedented, simple one-step procedure involving an atom-economically favorable, non-catalytic C−H activation reaction at room temperature from novel 1,2,4-trisguanidino-benzene molecules and 1,4-benzenedithiol. We then apply similar protocols to introduce other substituents in 5-position of a 1,2,4-trisguanidino-benzene molecule, demonstrating the scope of these exceptional C−H activation reactions. Finally, we report the synthesis of a hexakisguanidino-biphenyl by direct coupling of two trisguanidino-benzene units through C−H activation. Its oxidation leads to the first mixed-valence compound with charge delocalization between two redox-active guanidino units. The redox states of the resulting novel compounds are systematically studied.
Item Description:Gesehen am 07.06.2022
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.202200349

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