Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst.
Development of triazine-based esterifying reagents containing pyridines as a nucleophilic catalyst.
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DOI：
10.1039/c8ob01660g
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发表时间：
2018-09
影响因子：
3.2
通讯作者：
Kohei Yamada;Jie Liu;M. Kunishima
中科院分区：
文献类型：
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作者：
Kohei Yamada;Jie Liu;M. Kunishima
我们已经开发了新的基于三嗪的缩合试剂，其包含可以充当亲核催化剂的吡啶。1-（4，6-二甲氧基-1，3，5-三嗪-2-基）-3，5-二甲基吡啶鎓氯化物（DMT-3，5-LUT）对羧酸和醇的脱水缩合反应具有上级活性。DMT-3，5-LUT与羧酸的反应产生酰氧基三嗪的中间体，已知其对醇表现出适度的反应性，伴随着3，5-二甲基吡啶的释放。酰氧基三嗪和醇随后向酯的化学转化可以通过作为亲核催化剂的3，5-二甲基吡啶的作用来加速。详细的反应机理所揭示的反应的时程分析进行了讨论。
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.