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

作　　者：Xiaoqian He Kangbao Zhong Dan Heng Zhen Zeng Hao Ni Ruopeng Bai Yu Lan 

机构地区：[1]School of Chemistry and Chemical Engineering,Chongqing Key Laboratory of Theoretical and Computational Chemistry,Chongqing University,Chongqing 400030,China [2]College of Chemistry and Institute of Green Catalysis,Zhengzhou University,Zhengzhou 450001,China

出　　处：《Chinese Chemical Letters》2022年第4期2031-2035,共5页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China (Nos. 21822303, 21772020 and 22003006);a project (No. 2018CDXZ0002) supported by the Fundamental Research Funds for the Central Universities (Chongqing University);supported by the Graduate Research and Innovation Foundation of Chongqing,China (No. CYB20045)。

摘　　要：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, direct1,5-annulation was favored over the Cu-assisted annulation pathway. Furthermore, the regioselectivity for1,5-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.

关 键 词：Carbene precursor Regioselectivity DFT calculations Cyclopentaindol C3-alkylation 

分 类 号：O624.12[理学—有机化学]