Photoinduced Deoxygenative Halocarbocyclization of Aldehyde Enabled by Tertiary Phosphine
Abstract
The development of transition-metal-free protocols for the deoxygenative difunctionalization of carbonyls represents a significant challenge in organic synthesis. Herein, we report a photochemical strategy for deoxygenative difunctionalization of γ-enal by leveraging the reactivity of phosphine–iodide EDA complexes. Mechanistic studies indicate that the reaction proceeds through single-electron transfer within EDA complexes, addition of the fluoroalkyl radical to a C═C bond, 5- exo -trig cyclization, radical–radical cross-coupling between an in situ -generated alkoxy radical and phosphine radical cation, and S N 2 substitution. This method features a broad substrate scope and high step economy, offering a robust platform for the rapid assembly of complex functionalized carbocycles.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 21
- Pages
- 6828–6834
- Publication date
- 18 May 2026
- Language
- EN