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.
Original language | English |
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Pages (from-to) | 18803-18809 |
Number of pages | 7 |
Journal | Journal of the American Chemical Society |
Volume | 144 |
Issue number | 41 |
DOIs | |
Publication status | Published - 19 Oct 2022 |
Externally published | Yes |
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Huang, H., & Lambert, T. H. (2022). Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins. Journal of the American Chemical Society, 144(41), 18803-18809. https://doi.org/10.1021/jacs.2c08951