Journal
ORGANIC LETTERS
Volume 22, Issue 9, Pages 3728-3733Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01235
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Funding
- Department of Science and Technology (DST/SERB) [EMR/2016/007042]
- CSIR [0333/NS-EMRII]
- IIT Guwahati
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A visible-light-induced synthesis of N-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 tert-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 N-hydroxybenzimidoyl cyanide are also illustrated.
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