Intramolecular Acyl-Migration for Acyloxyselenenylation of Alkenes Promoted by Oxone DOI

Wen Xia,

Pei Tian,

Xiaohui Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

A novel green methodology for the Oxone-mediated oxidative addition of alkenes via intramolecular acyl migration has been developed. This transformation utilizes N-acyl-N-sulfonyl allylamines and diselenides as starting materials, with Oxone serving oxidant water a partial oxygen source. The protocol enables synthesis series β-acyloxy-γ-selenyl sulfonamides high to excellent yields demonstrates broad substrate scope. Notably, yield was maintained in gram-scale experiments, highlighting scalability this method. Through comprehensive control we have elucidated reaction mechanism, which involves rapid radical generation, predominant cationic pathway, migration. study presents an efficient environmentally benign approach valuable sulfonamides.

Language: Английский

Intramolecular Acyl-Migration for Acyloxyselenenylation of Alkenes Promoted by Oxone DOI

Wen Xia,

Pei Tian,

Xiaohui Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

A novel green methodology for the Oxone-mediated oxidative addition of alkenes via intramolecular acyl migration has been developed. This transformation utilizes N-acyl-N-sulfonyl allylamines and diselenides as starting materials, with Oxone serving oxidant water a partial oxygen source. The protocol enables synthesis series β-acyloxy-γ-selenyl sulfonamides high to excellent yields demonstrates broad substrate scope. Notably, yield was maintained in gram-scale experiments, highlighting scalability this method. Through comprehensive control we have elucidated reaction mechanism, which involves rapid radical generation, predominant cationic pathway, migration. study presents an efficient environmentally benign approach valuable sulfonamides.

Language: Английский

Citations

0