Deep Eutectic Solvents in Chemical Synthesis: Probing Solvent-Substrate Interactions

Volatile organic solvents are used in the majority of chemical syntheses but due to their adverse effects on health and the environment, replacements are sought. Recent work on deep eutectic solvents (DES) has demonstrated that these novel liquids can replace organic solvents and bring exciting advantages. In addition to being inexpensive, non-flammable and having a low volatility it has been shown that reactions using organolithium reagents in DES can be carried out at room temperature in air, in the presence of water - conditions that are normally incompatible with polar organometallic compounds. Reactions in DES also had improved yields and better selectivities than standard inert atmosphere protocols. Here we wish to probe DES-substrate and DES-product interactions for a model ketone used in an arylation reaction with phenyl-lithium to understand how DES promote these reactions.

绝大多数化学合成反应均使用挥发性有机溶剂，但鉴于其对人体健康与生态环境存在不利影响，开发替代溶剂的需求日益迫切。近年来针对低共熔溶剂（deep eutectic solvents，DES）的研究表明，这类新型液态介质可替代传统有机溶剂，并具备诸多极具吸引力的优势。除了廉价易得、不易燃且挥发性极低之外，研究证实，在DES中进行的有机锂试剂反应，可在室温、空气氛围且有水存在的条件下开展——而这类反应条件通常与极性有机金属化合物的反应体系不相兼容。相较于标准惰性气氛反应规程，在DES中进行的反应还可获得更高的产率与更优的选择性。本研究旨在针对一例与苯基锂发生芳基化反应的模型酮类底物，探究DES与底物、DES与产物之间的相互作用，以阐明DES促进此类反应的内在机制。