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Issue 35, 2018
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Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst

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Abstract

We have developed new triazine-based esterifying reagents comprising pyridines that can act as a nucleophilic catalyst. 1-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-3,5-lutidinium chloride (DMT-3,5-LUT) was found to exhibit a superior reactivity for the dehydrating condensation reaction between carboxylic acids and alcohols. The reaction of DMT-3,5-LUT with carboxylic acids produces intermediacy of acyloxytriazines, which is known to exhibit moderate reactivity toward alcohols, with concomitant liberation of 3,5-lutidine. The subsequent chemical transformation of the acyloxytriazines and alcohols into esters can be accelerated by the action of 3,5-lutidine as a nucleophilic catalyst. The detailed reaction mechanism revealed by a time-course analysis of the reactions is also discussed.

Graphical abstract: Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst

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Publication details

The article was received on 13 Jul 2018, accepted on 20 Aug 2018 and first published on 21 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01660G
Citation: Org. Biomol. Chem., 2018,16, 6569-6575
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    Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst

    K. Yamada, J. Liu and M. Kunishima, Org. Biomol. Chem., 2018, 16, 6569
    DOI: 10.1039/C8OB01660G

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