Radical-mediated direct C–H amination of arenes with secondary amines

Cosgrove, Sebastian C.; Plane, John M. C.; Marsden, Stephen P.

Abstract

Aryl dialkyl amines, valuable subunits of a wide range of effect chemicals, are accessed by intramolecular amination of aromatic C–H bonds employing UV photolysis of N-chloroamines. The reactions show good functional group tolerance and allow access to a range of fused and bridged polycyclic structures. The homogeneous reaction conditions allow for the one-pot conversion of secondary amines to their arylated derivatives. Experimental and theoretical evidence supports the involvement of electrophilic aminium radicals which react via direct ortho-attack on the arene.

Citation

Cosgrove, S. C., Plane, J. M. C., & Marsden, S. P. (2018). Radical-mediated direct C–H amination of arenes with secondary amines. Chemical Science, 9(32), 6647-6652. https://doi.org/10.1039/c8sc01747f

• Journal Article Type: Article
• Acceptance Date: Jul 10, 2018
• Publication Date: Jul 11, 2018
• Deposit Date: Jun 16, 2023
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Electronic ISSN: 2041-6539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 9
• Issue: 32
• Pages: 6647-6652
• DOI: https://doi.org/10.1039/c8sc01747f
• Keywords: General Chemistry
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Sebastian C. Cosgrove (ORCID); : John M. C. Plane (ORCID); : Stephen P. Marsden (ORCID); : Single-blind; : Received 17 April 2018; Accepted 10 July 2018; Accepted Manuscript published 11 July 2018; Advance Article published 16 July 2018; Version of Record published 15 August 2018