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Issue 33, 2016
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An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan

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Abstract

Synthesis of the dyes 3,3′-(arylmethylene)bis(2-hydroxynaphthalene-1,4-diones) was achieved efficiently in mild and metal-free conditions from a pseudo three-component reaction between 2-hydroxynaphthalene-1,4-dione and aldehydes under catalysis of O-carboxymethyl chitosan as a green, available, low-cost, and water-soluble bio-derived catalyst. This method combines the advantages of homogeneous catalysis in aqueous medium with convenient recovery and repeated recycling of the polymeric catalyst. The catalytic action of O-carboxymethyl chitosan is reminiscent of soft catalysis of enzymes and seems to be exerted by proton donating and accepting functions of the ammonium and amino groups arranged along the backbone of the polymeric bio-inspired catalyst.

Graphical abstract: An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan

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Publication details

The article was received on 12 Dec 2015, accepted on 08 Mar 2016 and first published on 10 Mar 2016


Article type: Paper
DOI: 10.1039/C5RA26580K
Citation: RSC Adv., 2016,6, 27388-27394

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    An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan

    F. Asghari-Haji, K. Rad-Moghadam and N. O. Mahmoodi, RSC Adv., 2016, 6, 27388
    DOI: 10.1039/C5RA26580K

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