Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

Peng Sun; Jiaojiao Yang; Zirui Song; Yichao Cai; Yajie Liu; Chunxia Chen; Xin Chen; Jinsong Peng

doi:10.1055/s-0039-1690240

Synthesis, Table of Contents

Synthesis 2020; 52(01): 75-84
DOI: 10.1055/s-0039-1690240

paper

Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

Peng Sun §

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

^bMaterial Science and Engineering College, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China

,

Jiaojiao Yang §

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

,

Zirui Song

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

,

Yichao Cai

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

,

Yajie Liu

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

,

Chunxia Chen∗

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

^bMaterial Science and Engineering College, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China

,

Xin Chen

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

^bMaterial Science and Engineering College, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China

,

Jinsong Peng ∗

^aCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, No. 26 Hexing Road, Harbin 150040, P. R. of China Email: ccx0109@nefu.edu.cn Email: jspeng1998@nefu.edu.cn

› Author Affiliations

Abstract

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^§ These authors contributed equally to this work

Abstract

Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl₂/phenanthroline, KMnO₄, and KHCO₃ at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted indoles in good to high yields.

Key words

copper-mediated - indoles - hydroamination - cross-dehydrogenative coupling - oxidation

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References

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