Ta Linda, Axelsson Anton, Bijl Joachim, Haukka Matti, Sundén Henrik
Chemistry and Biological Engineering, Chalmers University of Technology, Kemivägen 10, 412 96 Gothenburg (Sweden).
Chemistry. 2014 Oct 20;20(43):13889-93. doi: 10.1002/chem.201404288. Epub 2014 Sep 8.
Imidazolium-based ionic liquids (ILs) serve both as recyclable reaction media and as precatalysts for the N-heterocyclic carbene-catalyzed conjugate addition of α,β-unsaturated aldehydes to chalcones. The reaction produces a broad scope of 1,6-ketoesters incorporating an anti-diphenyl moiety in high yields and with high stereoselectivity. In recycling experiments, the IL can be reused up to five times with retained reactivity and selectivity. Moreover, the 1,6-ketoesters form self-assembled organogels in aliphatic hydrocarbons. The reaction protocol is robust, easily operated, scalable and highly functionalized compounds can be obtained from inexpensive and readily accessible starting materials.
基于咪唑鎓的离子液体（ILs）既作为可循环使用的反应介质，又作为氮杂环卡宾催化的α,β-不饱和醛与查耳酮的共轭加成反应的预催化剂。该反应能以高收率和高立体选择性生成多种含有反式二苯基部分的1,6-酮酯。在循环实验中，离子液体可重复使用多达五次，且仍保留反应活性和选择性。此外，1,6-酮酯在脂肪烃中形成自组装有机凝胶。该反应方案稳健、易于操作、可扩展，并且可以从廉价且易于获得的起始原料中获得高度官能化的化合物。
