Citation: Xiaoqian He, Kangbao Zhong, Dan Heng, Zhen Zeng, Hao Ni, Ruopeng Bai, Yu Lan. Is the metal involved or not? A computational study of Cu(I)-catalyzed [4 + 1] annulation of vinyl indole and carbene precursor[J]. Chinese Chemical Letters, ;2022, 33(4): 2031-2035. doi: 10.1016/j.cclet.2021.10.010 shu

Is the metal involved or not? A computational study of Cu(I)-catalyzed [4 + 1] annulation of vinyl indole and carbene precursor

Xiaoqian He ^a ,
Kangbao Zhong ^a ,
Dan Heng ^a ,
Zhen Zeng ^a ,
Hao Ni ^a ,
Ruopeng Bai ^{a, *,} ,
Yu Lan ^{a, b, *,}

a.
School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China
b.
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou 450001, China

ruopeng@cqu.edu.cn

lanyu@cqu.edu.cn

Received Date: 22 June 2021
Revised Date: 29 September 2021
Accepted Date: 9 October 2021
Available Online: 15 October 2021

Figures(7)

The Cu(I)-catalyzed [4 + 1] annulation of vinyl indoles and a carbene precursor is a powerful method for constructing cyclopentaindole derivatives. Density functional theory (DFT) calculations were used to elucidate the mechanism and regioselectivity of this reaction. After Cu-assisted indole C3-alkylation, direct 1,5-annulation was favored over the Cu-assisted annulation pathway. Furthermore, the regioselectivity for 1,5-annulation was attributed to the generated five-membered-ring product being more stable than the three-membered-ring product from 1,3-annulation, which was the kinetically favored pathway.
- Carbene precursor,
- Regioselectivity,
- DFT calculations,
- Cyclopentaindol,
- C3-alkylation
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