Citation: Yong Wang, Xinyi Cao, Jingfei Ji, Xiuling Cui, Chao Pi, Leyao Zhao, Yangjie Wu. Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes[J]. Chinese Chemical Letters, ;2021, 32(5): 1696-1700. doi: 10.1016/j.cclet.2020.12.026 shu

Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes

Yong Wang ^a ,
Xinyi Cao ^b ,
Jingfei Ji ^b ,
Xiuling Cui ^{a, *,} ,
Chao Pi ^a ,
Leyao Zhao ^b ,
Yangjie Wu ^{a, *,}

a.
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450052, China
b.
International College, Zhengzhou University, Zhengzhou 450052, China

cuixl@zzu.edu.cn

wyj@zzu.edu.cn

Received Date: 29 September 2020
Revised Date: 14 December 2020
Accepted Date: 16 December 2020
Available Online: 20 December 2020

Figures(5)

A green tandem reaction, including insertion/aerobic oxidation/bisindolylation, starting from indoles and diazo compounds has been developed. The combination of water and fluorinated alcohol plays dual roles as solvent and promoter in this chemical transformation. Molecular oxygen in the air acts as an oxidant. 3, 3'-Bis(indolyl)methanes with quaternary carbon were produced under metal-free conditions. No any catalyst and additive were required. N₂ and water were released as sole by-products. Absence of water and fluorinated alcohol resulted in Wolff rearrangement product.
- Bis(indolyl)methanes,
- Diazo,
- Fluorinated alcohol,
- Indole,
- Water
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