Journal
ACS CATALYSIS
Volume 6, Issue 10, Pages 6853-6860Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01969
Keywords
photocatalysis; visible light; electron transfer; energy transfer; chemodivergence
Categories
Funding
- NSFC [21072044, 21672052]
- Henan Province [14IRTSTHN006, 152300410057]
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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.
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