The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benz­ylation, and Cyclization Reactions

Ziwei Huang; Zirui Lin; Jiexiong Mai; Shaohuan Lv; Feng Xie; Youxue Yuan; Wenbing Zhang; Fan Qian; Bin Li

doi:10.1055/a-1840-5768

Synthesis, Table of Contents

Synthesis 2022; 54(19): 4381-4391
DOI: 10.1055/a-1840-5768

paper

The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benzylation, and Cyclization Reactions

Authors

Ziwei Huang

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China
Zirui Lin

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China
Jiexiong Mai

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China
Shaohuan Lv

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China
Feng Xie∗

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China
Youxue Yuan

^bGuangdong Wamo New Material Technology Co., Ltd, Jiangmen 529020, Guangdong Province, P. R. China
Wenbing Zhang

^bGuangdong Wamo New Material Technology Co., Ltd, Jiangmen 529020, Guangdong Province, P. R. China
Fan Qian

^bGuangdong Wamo New Material Technology Co., Ltd, Jiangmen 529020, Guangdong Province, P. R. China
Bin Li∗

^aSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P. R. China

Abstract

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Abstract

A convenient and practical pathway to 2-cyano and 2-ester anilines is described via efficient and selective copper(II)-catalyzed reductive amination via hydrosilylation process. Both 2-cyano and 2-ester anilines were successfully synthesized with good functional group tolerance and high selectivity. The application of the 2-cyano and -iodine containing anilines was developed in the synthesis of indoloindole derivatives via CuSO₄-catalyzed N-benzylation and cyclization reaction in ‘one pot’. More interestingly, the photophysical property investigations of these 2-cyano and 2-ester containing anilines exhibit excellent fluorescent properties, which have great potential application in the development of interesting near-ultraviolet optical devices in the near future.

Key words

copper catalysis - hydrosilane - reductive amination - amines - indoloindole

Full Text

References

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Supplementary Material

Supporting Information (PDF)

The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benz­ylation, and Cyclization Reactions

Authors

The Synthesis and Application of 2-Cyano and -Ester Containing Anilines: Selective Copper-Catalyzed Reductive Amination, N-Benzylation, and Cyclization Reactions