Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch

Chenhao Zhang*, Sanliang Li, Filip Bureš, Richmond Lee, Xinyi Ye, Zhiyong Jiang

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    164 Citations (Scopus)

    Abstract

    An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.

    Original languageEnglish
    Pages (from-to)6853-6860
    Number of pages8
    JournalACS Catalysis
    Volume6
    Issue number10
    DOIs
    Publication statusPublished - 7 Oct 2016

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