cs6b01969_si_001.pdf (2.12 MB)
Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
journal contribution
posted on 2016-09-02, 00:00 authored by Chenhao Zhang, Sanliang Li, Filip Bureš, Richmond Lee, Xinyi Ye, Zhiyong JiangAn
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.
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cyclic voltammetry studiesreaction pH influencesdicyanopyrazine-derived chromophorelight photocatalysischemodivergent strategyVisible Light Photocatalytic Aerobic Oxygenationformylformanilide derivativesoxidative pathwayDPZchemodivergent methodelectrochemical propertiesindolereaction pHChemoselective SwitchMechanistic investigations
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