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Issue 22, 2019
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Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process

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Abstract

A new strategy for the preparation of CF3-containing multi-substituted benzene compounds via an amine-catalyzed reaction under metal-free and air-tolerant conditions was developed. This green reaction provides a functional group-controlled synthetic strategy, and the polysubstituted benzene derivatives were obtained in moderate to good yields. Using a tri-substituted alkene containing a cyano group as the starting material, CF3-functionalized benzene compounds with four adjacent substituents can be formed via a Rauhut–Currier (RC) reaction-triggered [3 + 3] cascade. When the cyano group is replaced with a benzoyl group, Michael-initialized [4 + 2] aromatization occurs, producing the corresponding CF3-benzene with five contiguous substituent groups. The reaction also features numerous advantages, including excellent chemo- and regioselectivity, extensive substrate scope, and environmentally friendly conditions. A simple conversion of an aldehyde into a terminal alkyne was also achieved, and the utility of this environmentally compatible method and the one-pot reaction was demonstrated by synthesizing a CF3-functionalized benzene–zidovudine hybrid.

Graphical abstract: Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process

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Publication details

The article was received on 31 Jul 2019, accepted on 18 Oct 2019 and first published on 22 Oct 2019


Article type: Paper
DOI: 10.1039/C9GC02694K
Green Chem., 2019,21, 6179-6186

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    Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process

    F. Peng, Q. Zhao, W. Huang, S. Liu, Y. Zhong, Q. Mao, N. Zhang, G. He and B. Han, Green Chem., 2019, 21, 6179
    DOI: 10.1039/C9GC02694K

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