Issue 2, 2022

Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide

Abstract

Photoredox-catalyzed generation of sulfonated oxazolines starting from N-allylamides, DABCO·(SO2)2, and aryldiazonium salts has been developed. A range of sulfonated oxazolines were obtained in moderate to good yields. This transformation involves the sequential insertion of sulfur dioxide, intermolecular sulfonylation of alkenes and intramolecular cyclization via a radical process. This protocol features good compatibility of functional groups and mild reaction conditions. Sulfonated oxazolines could be efficiently transformed into β-amino alcohol, which is an important moiety in pharmaceuticals.

Graphical abstract: Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide

Supplementary files

Article information

Article type
Research Article
Submitted
13 oct. 2021
Accepted
26 nov. 2021
First published
30 nov. 2021

Org. Chem. Front., 2022,9, 364-369

Photoredox-catalyzed synthesis of sulfonated oxazolines from N-allylamides through the insertion of sulfur dioxide

Z. Chen, H. Zhang, S. Zhou and X. Cui, Org. Chem. Front., 2022, 9, 364 DOI: 10.1039/D1QO01540K

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