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

Photoredox-catalyzed generation of sulfonated oxazolines starting from N-allylamides, DABCO center dot(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 beta-amino alcohol, which is an important moiety in pharmaceuticals.

Automated summary

A photoredox-catalyzed method for generating sulfonated oxazolines has been developed, involving sequential insertion of sulfur dioxide, intermolecular sulfonylation of alkenes, and intramolecular cyclization via a radical process. This protocol is characterized by good compatibility of functional groups and mild reaction conditions, and the sulfonated oxazolines can be efficiently transformed into beta-amino alcohols, which are important moieties in pharmaceuticals.