Radical-Mediated Tandem Functional Group Transfer, Desulfonylation, and Cyclization Reactions: Synthesis of Oxindoles
Abstract
Desulfonylative skeletal editing has emerged as a powerful strategy in modern organic synthesis; however, desulfonylation of sulfonamides remains underdeveloped. Furthermore, the integration of radical cascades with Truce-Smiles rearrangement for simultaneous skeleton construction and remote functional-group migration is rare. To address these challenges, we developed a visible-light photoredox-catalyzed desulfurization strategy that combines radical cyclization relay, Truce-Smiles rearrangement, and desulfurization-driven rearomatization to access oxindoles efficiently. The reaction proceeds through a radical 1,4-cyano migration-triggered cyclization/desulfurization cascade under mild conditions using readily available, bench-stable substrates. Notably, the protocol is not restricted to alkyl bromodifluoroacetates and is compatible with a broad range of bromoesters.
Fields of Study & Subjects
Radical Photochemical Reactions
Sulfur-Based Synthesis Techniques
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 32
- Pages
- 10954–10966
- Publication date
- 30 July 2026
- Language
- EN