TY - DATA T1 - Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch PY - 2016/09/02 AU - Chenhao Zhang AU - Sanliang Li AU - Filip BuresĖŒ AU - Richmond Lee AU - Xinyi Ye AU - Zhiyong Jiang UR - https://acs.figshare.com/articles/journal_contribution/Visible_Light_Photocatalytic_Aerobic_Oxygenation_of_Indoles_and_pH_as_a_Chemoselective_Switch/3827502 DO - 10.1021/acscatal.6b01969.s001 L4 - https://ndownloader.figshare.com/files/5972652 KW - cyclic voltammetry studies KW - reaction pH influences KW - dicyanopyrazine-derived chromophore KW - light photocatalysis KW - chemodivergent strategy KW - Visible Light Photocatalytic Aerobic Oxygenation KW - formylformanilide derivatives KW - oxidative pathway KW - DPZ KW - chemodivergent method KW - electrochemical properties KW - indole KW - reaction pH KW - Chemoselective Switch KW - Mechanistic investigations N2 - 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. ER -