Iron-Promoted Construction of Indoles via Intramolecular Oxidative C–N Coupling of 2-Alkenylanilines Using Persulfate

Menglan Wang; Yudong Li; Qing-An Wu; Shuping Luo; Yuehui Li

doi:10.1055/s-0037-1611521

Synthesis, Table of Contents

Synthesis 2019; 51(16): 3085-3090
DOI: 10.1055/s-0037-1611521

paper

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C–N Coupling of 2-Alkenylanilines Using Persulfate

Menglan Wang

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: qawu@zjut.edu.cn

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: yhli@licp.cas.cn

,

Yudong Li

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: yhli@licp.cas.cn

,

Qing-An Wu*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: qawu@zjut.edu.cn

,

Shuping Luo

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: qawu@zjut.edu.cn

,

Yuehui Li*

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China Email: yhli@licp.cas.cn

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Abstract

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Abstract

Indole scaffold synthesis relies primarily on oxidative C–H amination of N-protected alkenylanilines for C–N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K₂S₂O₈ as oxidant in the presence of catalytic amounts of FeF₂. The K₂S₂O₈/FeF₂ system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.

Key words

indoles - C–N coupling - 2-alkenylanilines - oxidative amination - iron catalysis - 3-arylindoles - unprotected anilines

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References

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