Controllable Chemoselectivity With DPZ In Visible Light Aerobic Photooxygenation Of Indoles

Diverse and controllable pathways always enable the same set of starting materials to generate different products. The chemodivergent strategy can tremendously increase molecular diversity and complexity, and has been recognized as one of the most promising paradigms in organic and medicinal chemistry. To date, however, the chemodivergent variants in visible light photoredox catalysis are always limited in modulating reactants in the transformation process.In this thesis, we have developed a novel and efficient chemodivergent strategy in photocatalysis using low-energy and operationally convenient visible light. Through modulating reaction additives, the electrochemical properties of the photocatalyst DPZ could be conveniently regulated, allowing the first catalytic aerobic photooxygenation of indoles to undergo either SET(O₂^·-) or ET?¹O₂? process. As a result, two series of significant N-heterocyclic compounds, i.e. isatins and formylformanilides?or tryptanthrin?, were obtained in satisfactory yields. This methodology is also suitable to furnish photooxygenation of 2-subsituted indoles, providing expedient ways for the synthesis of four series of valuable N-containing molecules, especially including 2-methoxy 3-oxindoles and 2-substituted benzoxazinones.We trust that this investigation will benefit general audience in the fields of photocatalysis, synthetic organic chemistry, and pharmaceutical chemistry:1. This is the first chemodivergent protocol through tuning the electrochemical properties of the photocatalyst; 2. This is the first example of chemodivergence between electron transfer and energy transfer in visible light photocatalysis; 3. This is the first aerobic photooxygenation of indoles and 2-substituted indoles under the irradiation of low-energy visible light; 4. A series of N-heterocyclic molecules with highly important biological properties, such as isatins, formylformanilides, tryptanthrin, 2-methoxy 3-oxindoles, and benzoxazinones et al., were expediently synthesized in satisfactory results;...