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A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate

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Abstract

Visible-light-induced triple-domino cyclization between aryl alkynoates and diethyl bromomalonate was developed for the synthesis of indeno-coumarins. This one-pot method substantially simplified the production process for indeno-coumarins and a series of indeno-coumarins could be isolated in moderate to high yields. It was found that the obtained indeno-coumarins could be used as additional photosensitizers to initiate this transformation. A possible radical mechanism accompanying the processes of electron transfer and energy transfer is proposed based on the results of ESI-MS analysis, cyclic voltammetry, Stern–Volmer quenching experiments and control experiments. The photoluminescence properties (emission spectra and quantum yields) of the obtained indeno-coumarins were investigated.

Graphical abstract: A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate

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Publication details

The article was received on 23 Jun 2019, accepted on 28 Jul 2019 and first published on 29 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00795D
Org. Chem. Front., 2019, Advance Article

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    A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate

    Q. Li, Y. Yin, Y. Li, J. Zhang, M. Huang, J. K. Kim and Y. Wu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00795D

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