Electrochemically Driven, p K a -Controlled Regioselective Selenocyclization: Synthesis of Isocoumarin-1-imines with Structural Validation
Abstract
This study presents an electrochemical strategy that leverages the p K a of N -substituents to achieve precise regiocontrol in the selenocyclization of 2-alkynylbenzamides, providing efficient access to 4-selenyl isocoumarin-1-imines. This method successfully overcomes the longstanding selectivity challenges between competitive O / N -attack cyclization pathways. Crucially, the structure of the O -cyclized product was unambiguously confirmed by X-ray crystallographic analysis. Density functional theory (DFT) calculations further rationalize the observed high regioselectivity, revealing a significantly lower energy barrier for the O -attack pathway. The gram-scale synthesis and preliminary bioassays for fungicidal activity demonstrate the potential applications of this method.
Fields of Study & Subjects
Radical Photochemical Reactions
Organoselenium and organotellurium chemistry
Catalytic Alkyne Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 20
- Pages
- 6361–6365
- Publication date
- 7 May 2026
- Language
- EN