Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

An efficient visible light induced rhodium(I)‐catalyzed regioselective borylation of aromatic C−H bonds is reported. The photocatalytic system is based on a single NHC−RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating natur...

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Bibliographic Details
Published in:Angewandte Chemie 2019-10, Vol.131 (43), p.15388-15392
Main Authors: Thongpaen, Jompol, Manguin, Romane, Dorcet, Vincent, Vives, Thomas, Duhayon, Carine, Mauduit, Marc, Baslé, Olivier
Format: Article
Language:English
Subjects:
Bor
C-H-Aktivierung
Carbene
Chelation
Chemistry
Diodes
Hydrogen bonds
Irradiation
Photocatalysis
Photochemie
Radiation
Rhodium
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Summary:An efficient visible light induced rhodium(I)‐catalyzed regioselective borylation of aromatic C−H bonds is reported. The photocatalytic system is based on a single NHC−RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC‐carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C−H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII‐hydride intermediate. Doppel‐Agent: Eine durch sichtbares Licht induzierte RhI‐katalysierte regioselektive Borylierung von aromatischen C‐H‐Bindungen wurde entwickelt. Das photokatalytische System basiert auf einem NHC‐RhI‐Komplex, der sowohl das sichtbare Licht ernten als auch die Bindungsspaltung/‐bildung bei Raumtemperatur ermöglichen kann. Die zweizähnige Struktur des NHC‐Liganden erwies sich für die Stabilität und Reaktivität des RhI‐Komplexes als entscheidend.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201905924