One-pot, two-step synthesis and photophysical properties of 2-(5-phenylindol-3-yl)benzimidazole derivatives

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Author(s)
Lyu, Liu
Cai, Liu
Wang, Yun
Huang, Jinfeng
Zeng, Xiangchao
Liu, Porun
Year published
2017
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An efficient one-pot, two-step procedure has been successfully applied for the synthesis of a series of 2-(5-phenylindol-3-yl)benzimidazoles. The first step was cyclocondensation–oxidation of 5-bromoindole-3-aldehydes with o-phenylenediamines in 1,4-dioxane, which was promoted by activated carbon and used atmospheric air as a “green” oxidant. The resulting 2-(5-bromoindol-3-yl)benzimidazoles in the pot were in situ coupled with postadded phenylboronic acids, and catalyzed with PdCl2(dppf) in 1,4-dioxane-H2O to afford the desired compounds with satisfactorily high yields. The relationship between the synthesized compounds' ...
View more >An efficient one-pot, two-step procedure has been successfully applied for the synthesis of a series of 2-(5-phenylindol-3-yl)benzimidazoles. The first step was cyclocondensation–oxidation of 5-bromoindole-3-aldehydes with o-phenylenediamines in 1,4-dioxane, which was promoted by activated carbon and used atmospheric air as a “green” oxidant. The resulting 2-(5-bromoindol-3-yl)benzimidazoles in the pot were in situ coupled with postadded phenylboronic acids, and catalyzed with PdCl2(dppf) in 1,4-dioxane-H2O to afford the desired compounds with satisfactorily high yields. The relationship between the synthesized compounds' absorption, and fluorescence spectra with molecular structures has been investigated with experimental data and theoretical calculations.
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View more >An efficient one-pot, two-step procedure has been successfully applied for the synthesis of a series of 2-(5-phenylindol-3-yl)benzimidazoles. The first step was cyclocondensation–oxidation of 5-bromoindole-3-aldehydes with o-phenylenediamines in 1,4-dioxane, which was promoted by activated carbon and used atmospheric air as a “green” oxidant. The resulting 2-(5-bromoindol-3-yl)benzimidazoles in the pot were in situ coupled with postadded phenylboronic acids, and catalyzed with PdCl2(dppf) in 1,4-dioxane-H2O to afford the desired compounds with satisfactorily high yields. The relationship between the synthesized compounds' absorption, and fluorescence spectra with molecular structures has been investigated with experimental data and theoretical calculations.
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Journal Title
RSC Advances
Volume
7
Issue
78
Copyright Statement
© 2017 Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Subject
Chemical Sciences not elsewhere classified
Chemical Sciences