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Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
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| Zeitschriftentitel: | Angewandte Chemie |
|---|---|
| Personen und Körperschaften: | , , , , , , |
| In: | Angewandte Chemie, 131, 2019, 38, S. 13452-13456 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. |
|---|---|
| author |
Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. |
| spellingShingle |
Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. Angewandte Chemie Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication General Medicine |
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huang, he |
| spelling |
Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.201906381 <jats:title>Abstract</jats:title><jats:p>Visible‐light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited‐state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single‐electron transfer (SET), resulting in C−H/N−H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the <jats:italic>cis</jats:italic>‐2,6‐dimethylpiperidine moieties.</jats:p> Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication Angewandte Chemie |
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| title |
Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
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Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
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Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_fullStr |
Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
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Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
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Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
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electrophotocatalysis with a trisaminocyclopropenium radical dication |
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General Medicine |
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http://dx.doi.org/10.1002/ange.201906381 |
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2019 |
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13452-13456 |
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<jats:title>Abstract</jats:title><jats:p>Visible‐light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited‐state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single‐electron transfer (SET), resulting in C−H/N−H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the <jats:italic>cis</jats:italic>‐2,6‐dimethylpiperidine moieties.</jats:p> |
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| author | Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, Lambert, Tristan H. |
| author_facet | Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, Lambert, Tristan H., Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, Lambert, Tristan H. |
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| description | <jats:title>Abstract</jats:title><jats:p>Visible‐light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited‐state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single‐electron transfer (SET), resulting in C−H/N−H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the <jats:italic>cis</jats:italic>‐2,6‐dimethylpiperidine moieties.</jats:p> |
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| spelling | Huang, He Strater, Zack M. Rauch, Michael Shee, James Sisto, Thomas J. Nuckolls, Colin Lambert, Tristan H. 0044-8249 1521-3757 Wiley General Medicine http://dx.doi.org/10.1002/ange.201906381 <jats:title>Abstract</jats:title><jats:p>Visible‐light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited‐state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single‐electron transfer (SET), resulting in C−H/N−H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the <jats:italic>cis</jats:italic>‐2,6‐dimethylpiperidine moieties.</jats:p> Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication Angewandte Chemie |
| spellingShingle | Huang, He, Strater, Zack M., Rauch, Michael, Shee, James, Sisto, Thomas J., Nuckolls, Colin, Lambert, Tristan H., Angewandte Chemie, Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication, General Medicine |
| title | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_full | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_fullStr | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_full_unstemmed | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_short | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| title_sort | electrophotocatalysis with a trisaminocyclopropenium radical dication |
| title_unstemmed | Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication |
| topic | General Medicine |
| url | http://dx.doi.org/10.1002/ange.201906381 |