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Photocarboxylation of Benzylic C-H bonds
Meng, Qing-Yuan
, Schirmer, Tobias, Berger, Anna Lucia, Donabauer, Karsten und König, Burkhard
(2019)
Photocarboxylation of Benzylic C-H bonds.
Journal of the American Chemical Society 141, S. 11393-11397.
Veröffentlichungsdatum dieses Volltextes: 09 Jul 2019 08:59
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.40471
Zusammenfassung
The carboxylation of sp(3)-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of ...
The carboxylation of sp(3)-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.
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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Journal of the American Chemical Society | ||||
| Verlag: | AMER CHEMICAL SOC | ||||
|---|---|---|---|---|---|
| Ort der Veröffentlichung: | WASHINGTON | ||||
| Band: | 141 | ||||
| Seitenbereich: | S. 11393-11397 | ||||
| Datum | 2019 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identifikationsnummer |
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| Stichwörter / Keywords | CARBON-DIOXIDE; VISIBLE-LIGHT; CATALYZED CARBOXYLATION; REDUCTION POTENTIALS; ALKENES; CO2; CARBONYLATION; RADICALS; HALIDES; SYSTEM; | ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-404717 | ||||
| Dokumenten-ID | 40471 |
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