Issue 47, 2020

A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry

Abstract

The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C–P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process.

Graphical abstract: A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry

Supplementary files

Article information

Article type
Edge Article
Submitted
09 8 2020
Accepted
20 10 2020
First published
20 10 2020
This article is Open Access

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

Chem. Sci., 2020,11, 12822-12828

A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry

T. Constantin, F. Juliá, N. S. Sheikh and D. Leonori, Chem. Sci., 2020, 11, 12822 DOI: 10.1039/D0SC04387G

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