A visible-light-induced synthesis of -hydroxybenzimidoyl cyanides from aromatic terminal alkenes is achieved by using Eosin Y as an organic photoredox catalyst. The process goes via a radical pathway with successive incorporation of two nitrogen atoms, one each from -butyl nitrite and ammonium acetate. The final product is achieved by the concomitant installation of an oxime and a nitrile group. DFT calculation supports a biradical pathway and all the proposed steps. A few useful synthetic transformations of -hydroxybenzimidoyl cyanide are also illustrated.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.0c01235 | DOI Listing |
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!