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Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins

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Abstract

We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(II)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.

Graphical abstract: Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins

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Publication details

The article was received on 05 Mar 2019, accepted on 02 Apr 2019 and first published on 03 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC01801H
Citation: Chem. Commun., 2019, Advance Article

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    Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins

    A. Ragupathi, A. Sagadevan, V. P. Charpe, C. Lin, J. Hwu and K. C. Hwang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC01801H

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