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Issue 4, 2019
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δ C–H (hetero)arylation via Cu-catalyzed radical relay

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Abstract

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

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Supplementary files

Article information


Submitted
02 Oct 2018
Accepted
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

Chem. Sci., 2019,10, 1207-1211
Article type
Edge Article

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

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