Issue 4, 2019

δ C–H (hetero)arylation via Cu-catalyzed radical relay


A Cu-catalyzed strategy has been developed that harnesses a radical relay mechanism to intercept a distal C-centered radical for C–C bond formation. This approach enables selective δ C–H (hetero)arylation of sulfonamides via intramolecular hydrogen atom transfer (HAT) by an N-centered radical. The radical relay is both initiated and terminated by a Cu catalyst, which enables incorporation of arenes and heteroarenes by cross-coupling with boronic acids. The broad scope and utility of this catalytic method for δ C–H arylation is shown, along with mechanistic probes for selectivity of the HAT mechanism. A catalytic, asymmetric variant is also presented, as well as a method for accessing 1,1-diaryl-pyrrolidines via iterative δ C–H functionalizations.

Graphical abstract: δ C–H (hetero)arylation via Cu-catalyzed radical relay

Supplementary files

Article information

Article type
Edge Article
02 Oct 2018
09 Nov 2018
First published
09 Nov 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 1207-1211

δ C–H (hetero)arylation via Cu-catalyzed radical relay

Z. Zhang, L. M. Stateman and D. A. Nagib, Chem. Sci., 2019, 10, 1207 DOI: 10.1039/C8SC04366C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity