Expedient Access to Structural Complexity via Radical β-Fragmentation of N‒O Bond

Structures containing N‒O bonds have been well established as precursors for nitrogen- and/or oxygen-centered radicals under visible light conditions in modern organic synthesis. While both heterolytic and homolytic scission of N‒O bonds have been extensively documented, intrinsic limitations related to substrate structure somewhat restrict their broader application. This paper highlights a novel strategy that synergistically combines a radical generation process independent of the substrate's redox potential, with a radical-induced β-fragmentation of the N‒O bond. Subsequent manipulation of the generated nitrogen- or oxygen-centered radicals leads to the successful development of group-transfer carboamination of alkenes, ring-opening functionalization of heterocycles, and efficient trifunctionalization of unactivated alkenes.

Publication History

Received: 07 November 2024

Accepted after revision: 17 December 2024

Accepted Manuscript online:
17 December 2024