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.

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http://dx.doi.org/10.1021/acs.orglett.0c01235DOI Listing

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