Vetica Fabrizio, Bortolami Martina, Petrucci Rita, Rocco Daniele, Feroci Marta
Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185, Rome, Italy.
Department of Basic and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, Via Castro Laurenziano 7, 00161, Rome, Italy.
Chem Rec. 2021 Sep;21(9):2130-2147. doi: 10.1002/tcr.202000178. Epub 2021 Jan 28.
In the last twenty years, N-heterocyclic carbenes (NHCs) have been extensively studied for their application as organocatalysts in stereoselective synthesis as well as ligands for transition metals-promoted synthetic methodologies. Derived mainly from azolium salts, NHCs have demonstrated exceptional versatility in their generation usually performed by deprotonation or reduction (chemical or electrochemical). In particular, the generation of NHC under electrochemical conditions, starting from azolium-based ionic liquids, has proven to be a successful green approach and demonstrated wide applicability in organic synthesis. In this Personal Account, the application of electrogenerated NHCs in organic synthesis will be discussed, with a particular attention to the different reactivity in ionic liquids compared to classical organic solvents.
在过去的二十年中，N-杂环卡宾（NHCs）因其作为有机催化剂在立体选择性合成中的应用以及作为过渡金属促进的合成方法的配体而受到广泛研究。NHCs主要衍生自唑鎓盐，在通过去质子化或还原（化学或电化学）进行的生成过程中表现出非凡的通用性。特别是，从基于唑鎓盐的离子液体开始，在电化学条件下生成NHC已被证明是一种成功的绿色方法，并在有机合成中显示出广泛的适用性。在这篇个人综述中，将讨论电生成的NHC在有机合成中的应用，特别关注与传统有机溶剂相比在离子液体中的不同反应性。
