Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins

He Huang, Tristan H. Lambert*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

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 languageEnglish
Pages (from-to)18803-18809
Number of pages7
JournalJournal of the American Chemical Society
Volume144
Issue number41
DOIs
Publication statusPublished - 19 Oct 2022
Externally publishedYes

Fingerprint

Dive into the research topics of 'Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins'. Together they form a unique fingerprint.

Cite this

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