10.1021/acscatal.6b01969.s001
Chenhao Zhang
Chenhao
Zhang
Sanliang Li
Sanliang
Li
Filip Bureš
Filip
Bureš
Richmond Lee
Richmond
Lee
Xinyi Ye
Xinyi
Ye
Zhiyong Jiang
Zhiyong
Jiang
Visible Light Photocatalytic Aerobic Oxygenation of
Indoles and pH as a Chemoselective Switch
American Chemical Society
2016
cyclic voltammetry studies
reaction pH influences
dicyanopyrazine-derived chromophore
light photocatalysis
chemodivergent strategy
Visible Light Photocatalytic Aerobic Oxygenation
formylformanilide derivatives
oxidative pathway
DPZ
chemodivergent method
electrochemical properties
indole
reaction pH
Chemoselective Switch
Mechanistic investigations
2016-09-02 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Visible_Light_Photocatalytic_Aerobic_Oxygenation_of_Indoles_and_pH_as_a_Chemoselective_Switch/3827502
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.