Issue 2, 2011
From the journal:

Green Chemistry

Ambient carboxylation on a supported reversible CO2 carrier: ketone to β-keto ester

Eric J. Beckmana  and  Pradip Munshi*abc  

* Corresponding authors

a Chemical Engineering Department, University of Pittsburgh, Pittsburgh, USA
Fax: (412)624-9639
Tel: (412)624-4828

b Rubamin Laboratories Ltd., Dabhasa, Vadodara, Gujarat, India

c Research Centre, Reliance Industries Limited, Vadodara, Gujarat, India
E-mail: pradip.munshi@ril.com
Fax: +91 265 669 3937
Tel: +91 265 6696049

Abstract

A reversible CO2 carrier (RCC) has been developed to perform carboxylation of ketone to β-ketoester under ambient CO2 pressure and temperature. RCC has been synthesized by immobilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) on methylhydrosiloxane support and reacting with CO2 with 100% degree of functionalisation. RCC is found to be recyclable and shows retention of activity in 5 recycles. CO2 absorption under ambient temperature and desorption at 120 °C renders the material suitable for carrying out carboxylation reactions at 25 °C with excellent yields. The yield of the reaction can reach up to 100% with TON 200 in 4 h. The extent of the reaction primarily depends upon enol content of the substrate. β-Ketoacid produced during the reaction can be isolated and converted to its corresponding methyl ester derivative by reacting with methyl iodide.

Graphical abstract: Ambient carboxylation on a supported reversible CO2 carrier: ketone to β-keto ester

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Article information

DOI
https://doi.org/10.1039/C0GC00704H
Article type
Paper
Submitted
18 Oct 2010
Accepted
02 Dec 2010
First published
04 Jan 2011

Green Chem., 2011,13, 376-383

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Ambient carboxylation on a supported reversible CO2 carrier: ketone to β-keto ester

E. J. Beckman and P. Munshi, Green Chem., 2011, 13, 376 DOI: 10.1039/C0GC00704H

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