Journal
GREEN CHEMISTRY
Volume 21, Issue 22, Pages 6179-6186Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9gc02694k
Keywords
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Funding
- National Natural Science Foundation of China [81573588, 81773889, 21772131]
- Science & Technology Department of Sichuan Province [2017JZYD0001, 2017JY0323]
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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.
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