Preparation of Oxazole Acetals from N-Propargylamides Enabled by Visible-Light-Promoted Selenium-π-Acid Catalysis

An unprecedented catalytic system consisting of diselenides, Selectfluor and visible light has been developed for the one-pot synthesis of oxazole acetals from N-propargylamides and alcohols. This system shows the processes of cyclization, aromatization and acetalization, resulting in the construction of multiple carbon-oxygen bonds. These transformations demonstrate the excellent compatibility of visible-light promotion with organocatalytic oxidative carbon-oxygen bond formations using air as the terminal oxidant.

Automated summary

An unprecedented catalytic system has been developed for the one-pot synthesis of oxazole acetals from N-propargylamides and alcohols using diselenides, Selectfluor, and visible light. This system demonstrates excellent compatibility of visible-light promotion with organocatalytic oxidative carbon-oxygen bond formations, using air as the terminal oxidant.