Transition metal-free cross-dehydrogenative coupling acylation of coumarins by the K2S2O8/Aliquat 336 catalytic system: a versatile strategy towards 4-aroylcoumarin derivatives

Mehdi Adib; Rahim Pashazadeh; Saideh Rajai-Daryasarei; Roya Kabiri; Mehdi Jahani

doi:10.1039/C6RA26278C

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Transition metal-free cross-dehydrogenative coupling acylation of coumarins by the K₂S₂O₈/Aliquat 336 catalytic system: a versatile strategy towards 4-aroylcoumarin derivatives†

Mehdi Adib,*^a Rahim Pashazadeh,^a Saideh Rajai-Daryasarei,^a Roya Kabiri^b and Mehdi Jahani^a

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* Corresponding authors

^a School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
E-mail: madib@khayam.ut.ac.ir
Fax: +98 21 66495291
Tel: +98 21 66495291

^b NMR Lab, Faculty of Chemistry, Tabriz University, Tabriz, Iran

Abstract

A new and efficient transition metal-free oxidative cross-dehydrogenative coupling (CDC) reaction is described for the preparation of 4-aroylcoumarin derivatives. In this protocol aldehydes have been used as acylating agents for acylation of 3-substituted coumarins through C(sp²)–C(sp²) bond formation using the K₂S₂O₈/Aliquat 336 system as an inexpensive and environmentally friendly reagent. The reactions proceeded in acetonitrile at 80 °C for 2–3 h to afford the corresponding 4-aroylcoumarin derivatives in high yields.

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Article information

DOI: https://doi.org/10.1039/C6RA26278C
Article type: Paper
Submitted: 28 Sep 2016
Accepted: 15 Nov 2016
First published: 21 Nov 2016

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RSC Adv., 2016,6, 110656-110660

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Transition metal-free cross-dehydrogenative coupling acylation of coumarins by the K₂S₂O₈/Aliquat 336 catalytic system: a versatile strategy towards 4-aroylcoumarin derivatives

M. Adib, R. Pashazadeh, S. Rajai-Daryasarei, R. Kabiri and M. Jahani, RSC Adv., 2016, 6, 110656 DOI: 10.1039/C6RA26278C

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