Kulchat Sirinan, Lehn Jean-Marie
Laboratoire de Chimie Supramoléculaire, ISIS, Université de Strasbourg, 8 allée Gaspard Monge, 67000, Strasbourg, France.
Chem Asian J. 2015 Nov;10(11):2484-96. doi: 10.1002/asia.201500604. Epub 2015 Aug 19.
Dynamic covalent libraries (DCLs) of quaternary ammonium cations were set up by reversible nucleophilic substitution (S(N)2' and S(N)2) exchange reactions of ammonium salts and tertiary amines. The reactions were conducted at 60 °C to generate thermodynamically and kinetically controlled mixtures of quaternary ammonium compounds and tertiary amines, and were accelerated by using iodide as a nucleophilic catalyst. Microwave irradiation was used to assist the exchange reaction between the pyridinium salts and pyridine derivatives. Finally, experiments towards the generation of dynamic ionic liquids were performed. The results of this study pave the way for the extension of dynamic combinatorial chemistry to nucleophilic substitution reactions.
通过铵盐与叔胺的可逆亲核取代（S(N)2'和S(N)2）交换反应建立了季铵阳离子的动态共价库。反应在60°C下进行，以生成季铵化合物和叔胺的热力学和动力学控制混合物，并使用碘化物作为亲核催化剂来加速反应。微波辐射用于辅助吡啶鎓盐与吡啶衍生物之间的交换反应。最后，进行了生成动态离子液体的实验。本研究结果为将动态组合化学扩展到亲核取代反应铺平了道路。
