Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

Wen-Jun Zhou, Zhe-Hao Wang, Li-Li Liao, Yuan-Xu Jiang, Ke-Gong Cao, Tao Ju, Yiwen Li, Guang-Mei Cao and Da-Gang Yu ()
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Wen-Jun Zhou: Sichuan University
Zhe-Hao Wang: Sichuan University
Li-Li Liao: Sichuan University
Yuan-Xu Jiang: Sichuan University
Ke-Gong Cao: Sichuan University
Tao Ju: Sichuan University
Yiwen Li: Sichuan University
Guang-Mei Cao: Sichuan University
Da-Gang Yu: Sichuan University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-17085-9

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