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- Title
Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis.
- Authors
Zhou, Wen-Jun; Wang, Zhe-Hao; Liao, Li-Li; Jiang, Yuan-Xu; Cao, Ke-Gong; Ju, Tao; Li, Yiwen; Cao, Guang-Mei; Yu, Da-Gang
- Abstract
Catalytic reductive coupling of two electrophiles and one unsaturated bond represents an economic and efficient way to construct complex skeletons, which is dominated by transition-metal catalysis via two electron transfer. Herein, we report a strategy of visible-light photoredox-catalyzed successive single electron transfer, realizing dearomative arylcarboxylation of indoles with CO2. This strategy avoids common side reactions in transition-metal catalysis, including ipso-carboxylation of aryl halides and β-hydride elimination. This visible-light photoredox catalysis shows high chemoselectivity, low loading of photocatalyst, mild reaction conditions (room temperature, 1 atm) and good functional group tolerance, providing great potential for the synthesis of valuable but difficultly accessible indoline-3-carboxylic acids. Mechanistic studies indicate that the benzylic radicals and anions might be generated as the key intermediates, thus providing a direction for reductive couplings with other electrophiles, including D2O and aldehyde. Catalytic reductive coupling of two electrophiles and one C = C bond is usually performed by two electron transfer metal catalysis. Herein, the authors show a visible light photoredox-catalyzed successive single electron transfer leading to dearomative arylcarboxylation of indoles with CO2 and generating indoline-3-carboxylic acids.
- Subjects
ELECTRON-transfer catalysis; CATALYSIS; METAL-metal bonds; CHARGE exchange; RADICAL anions; INDOLE; ARYL halides
- Publication
Nature Communications, 2020, Vol 11, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-020-17085-9