Photoredox-Catalyzed Radical Cascade Reaction To Synthesize Fluorinated Pyrrolo[1,2‑d]benzodiazepine Derivatives

A new photoredox-catalyzed cascade reaction is described to access fluorinated pyrrolo­[1,2-d]­benzodiazepine derivatives under mild conditions. In this process, single electron transfer (SET) between the excited state photocatalyst fac-Ir­(ppy)3 and ethyl bromodifluoroacetate initiated the regiosel...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-07, Vol.84 (14), p.9322-9329
Main Authors: Lian, Guifang, Li, Jingyu, Liu, Ping, Sun, Peipei
Format: Article
Language:English
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Summary:A new photoredox-catalyzed cascade reaction is described to access fluorinated pyrrolo­[1,2-d]­benzodiazepine derivatives under mild conditions. In this process, single electron transfer (SET) between the excited state photocatalyst fac-Ir­(ppy)3 and ethyl bromodifluoroacetate initiated the regioselective radical addition to a wide range of 2-(1H-pyrrol-1-yl) anilines or indol-substituted anilines, followed by another SET process and intramolecular amidation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00937