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. 2022 Jun 20;61(25):e202202971.
doi: 10.1002/anie.202202971. Epub 2022 Apr 25.

Photoinduced α-C-H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay

Wongyu Lee  1   2 , Dongwook Kim  1   2 , Sangwon Seo  1   2 , Sukbok Chang  1   2
Affiliations

Photoinduced α-C-H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay

Wongyu Lee et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we report a polar-radical relay strategy for α-C-H amination of cyclic amines with N-chloro-N-sodio-carbamates. The relay is initiated by in situ generation of cyclic iminium intermediate using N-iodosuccinimide (NIS) oxidant as an initiator, which then operates through a series of polar (addition and elimination) and radical (homolysis, hydrogen- and halogen atom transfer) reactions to enable the challenging C-N bond formation in a controlled manner. A broad range of α-amino cyclic amines were readily accessed with excellent regioselectivity, and the superb applicability was further demonstrated by functionalization of biologically relevant compounds.

Keywords: Amination; Amines; Radicals; Reaction Mechanisms; Sustainability.

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