Selective Radical Amination of Aldehydic C(sp2)–H Bonds with Fluoroaryl Azides via Co(ii)-based Metalloradical Catalysis: Synthesis of N-fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions
Document Type
Article
Publication Date
2014
Digital Object Identifier (DOI)
https://doi.org/10.1039/C4SC00697F
Abstract
The Co(II) complex of the D2h-symmetric amidoporphyrin 3,5-DitBu-IbuPhyrin, [Co(P1)], has proven to be an effective metalloradical catalyst for intermolecular amination of C(sp2)–H bonds of aldehydes with fluoroaryl azides. The [Co(P1)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and nonoxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C–H amination is suitable for different combinations of aldehydes and fluoroaryl azides, producing the corresponding N-fluoroaryl amides in good to excellent yields. A series of mechanistic studies support a stepwise radical mechanism for the Co(II)-catalyzed intermolecular C–H amination.
Was this content written or created while at USF?
Yes
Citation / Publisher Attribution
Chemical Science, v. 5, p. 2422-2427
Scholar Commons Citation
Jin, Li-Mei; Lu, Hongjian; Cui, Yuan; Lizardi, Christopher L.; Arzua, Thiago N.; Wojtas, Lukasz; Cui, Xin; and Zhang, X. Peter, "Selective Radical Amination of Aldehydic C(sp2)–H Bonds with Fluoroaryl Azides via Co(ii)-based Metalloradical Catalysis: Synthesis of N-fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions" (2014). Chemistry Faculty Publications. 155.
https://digitalcommons.usf.edu/chm_facpub/155
