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

Chemical Science
Timothée ConstantinDaniele Leonori

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.

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Citations

Jun 12, 2021·Organic Letters·Lalita TanwarTobias Ritter
Dec 29, 2020·Journal of the American Chemical Society·Haoyu LiShunsuke Chiba
Aug 28, 2021·Chemical Science·Lewis CaigerDaniele Leonori
Oct 8, 2021·ACS Applied Materials & Interfaces·Jorge C Herrera-LunaRaúl Pérez-Ruiz
Nov 10, 2021·Organic & Biomolecular Chemistry·Constantine V MilyutinMikhail E Minyaev

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