Related Experiment Video
Updated: Aug 26, 2025

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
Published on: January 4, 2018
Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins
1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Abstract:
A method for the regiodivergent aminooxygenation of aryl olefins under electrophotocatalytic conditions is described. The procedure employs a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding oxazolines with high chemo- and diastereoselectivity. With the judicious choice between two inexpensive and abundant reagents, namely water and urethane, either 2-amino-1-ol or 1-amino-2-ol derivatives could be prepared from the same substrate. This method is amenable to multigram synthesis of the oxazoline products with low catalyst loadings.
Related Concept Videos
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Hydroboration-Oxidation of Alkenes
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Oxymercuration-Reduction of Alkenes

