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Electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes for the synthesis of tetrahydroquinolines

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Abstract

Heterocyclic compounds, especially nitrogen heterocycles, are one of the most important classes of compounds in the pharmaceutical and agrochemical industries. The oxidative [4 + 2] annulation reaction provides a powerful tool for the rapid construction of six-membered heterocycles. Herein, we report a metal- and external oxidant-free method for the uniform synthesis of tetrahydroquinolines through the electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes. In this strategy, one partner loses only two hydrogen atoms while another partner reduces one degree of unsaturation, accompanied by the generation of hydrogen. Under the conditions of an undivided cell and room temperature, a series of tetrahydroquinoline derivatives were prepared with good yields.

Graphical abstract: Electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes for the synthesis of tetrahydroquinolines

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Publication details

The article was received on 06 Aug 2018, accepted on 02 Oct 2018 and first published on 08 Oct 2018


Article type: Communication
DOI: 10.1039/C8GC02463D
Citation: Green Chem., 2018, Advance Article
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    Electrochemical oxidative [4 + 2] annulation of tertiary anilines and alkenes for the synthesis of tetrahydroquinolines

    P. Huang, P. Wang, S. Wang, S. Tang and A. Lei, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC02463D

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