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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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
01 April 2022
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| 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 |
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| 245 | 1 | 0 | |a Connecting organic redox-active building blocks through mild noncatalytic C−H activation |c Ute Wild, Olaf Hübner, Markus Enders, Elisabeth Kaifer, and Hans-Jörg Himmel |
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| 520 | |a 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. | ||
| 650 | 4 | |a C−H activation | |
| 650 | 4 | |a Electronic coupling | |
| 650 | 4 | |a Guanidines | |
| 650 | 4 | |a Oxidation | |
| 650 | 4 | |a Redox chemistry | |
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