Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
J Am Chem Soc. 2022 Oct 19;144(41):18803-18809. doi: 10.1021/jacs.2c08951. Epub 2022 Oct 4.
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.
本文描述了一种在光电催化条件下区域发散的芳基烯烃的氨氧化方法。该方法采用三氨基环丙烯鎓(TAC)离子催化剂,在受控电化学势下用可见光照射,将芳基烯烃高化学选择性和立体选择性地转化为相应的恶唑啉。通过明智地选择两种廉价且丰富的试剂,即水和氨基甲酸酯,可从同一底物制备 2-氨基-1-醇或 1-氨基-2-醇衍生物。该方法适用于在低催化剂负载下进行恶唑啉产物的多克合成。