Aryl radical-mediated N-heterocyclic carbene catalysis

Yuki Matsuki, Nagisa Ohnishi, Yuki Kakeno, Shunsuke Takemoto, Takuya Ishii, Kazunori Nagao () and Hirohisa Ohmiya ()
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Yuki Matsuki: Kanazawa University, Kakuma-machi
Nagisa Ohnishi: Kanazawa University, Kakuma-machi
Yuki Kakeno: Kanazawa University, Kakuma-machi
Shunsuke Takemoto: Kanazawa University, Kakuma-machi
Takuya Ishii: Kanazawa University, Kakuma-machi
Kazunori Nagao: Kanazawa University, Kakuma-machi
Hirohisa Ohmiya: Kanazawa University, Kakuma-machi

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract There have been significant advancements in radical reactions using organocatalysts in modern organic synthesis. Recently, NHC-catalyzed radical reactions initiated by single electron transfer processes have been actively studied. However, the reported examples have been limited to catalysis mediated by alkyl radicals. In this article, the NHC organocatalysis mediated by aryl radicals has been achieved. The enolate form of the Breslow intermediate derived from an aldehyde and thiazolium-type NHC in the presence of a base undergoes single electron transfer to an aryl iodide, providing an aryl radical. The catalytically generated aryl radical could be exploited as an arylating reagent for radical relay-type arylacylation of styrenes and as a hydrogen atom abstraction reagent for α-amino C(sp3)–H acylation of secondary amides.

Date: 2021
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DOI: 10.1038/s41467-021-24144-2

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