Details

Autor(en) / Beteiligte

• Li, Hang
• Li, Na
• Wu, Jinghao
• Yu, Tianyang
• Zhang, Ran
• Xu, Li-Ping
• Wei, Hao

Titel

Rhodium-Catalyzed Intramolecular Nitrogen Atom Insertion into Arene Rings

Ist Teil von

• Journal of the American Chemical Society, 2023-08, Vol.145 (32), p.17570-17576

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• In this study, we describe the direct insertion of an intramolecular nitrogen atom into an aromatic C–C bond. In this transformation, carbamoyl azides are activated by a Rh catalyst and subsequently directly inserted into the C–C bond of an arene ring to access fused azepine products. This transformation is challenging, owing to the existence of a competitive C–H amination pathway. The use of a paddlewheel dirhodium complex Rh2(esp)2 effectively inhibited the undesired C–H insertion. Density functional theory calculations were performed to reveal the reaction mechanism and origin of the chemoselectivity of the Rh-catalyzed reactions. The novel fused azepine products are highly robust and allow for downstream diversification.