Jacobs Emily, Nguyen Thanh Vinh
School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia.
Chemistry. 2025 Feb 25;31(12):e202402339. doi: 10.1002/chem.202402339. Epub 2025 Feb 5.
N-Heterocyclic carbenes (NHCs) have become important tools in modern synthetic chemistry due to their versatility as organocatalysts and ligands in organometallic complexes. Since their first isolation and characterization, NHCs have demonstrated significant utility in various catalytic processes, offering advantages such as strong σ-electron donation and the ability to stabilize reactive intermediates. However, beyond their well-documented roles in catalysis, the potential of NHCs as stoichiometric reagents and synthetic building blocks remains an underexplored yet promising area. This Mini-review aims to shed light on these lesser-known applications of NHCs and their N-heterocyclic precursors or derivatives in organic synthesis. Furthermore, we discuss how the unique electronic and steric properties of NHCs can be harnessed to develop new synthetic methodologies or construct interesting organic frameworks. By highlighting these emerging uses, we hope to encourage further research into the non-catalytic applications of NHCs, broadening their scope and impact in synthetic chemistry.
N-杂环卡宾（NHCs）因其作为有机催化剂和有机金属配合物中配体的多功能性，已成为现代合成化学中的重要工具。自首次分离和表征以来，NHCs在各种催化过程中已展现出显著的实用性，具有诸如强σ电子供体能力以及稳定反应中间体的能力等优势。然而，除了其在催化方面有充分记录的作用外，NHCs作为化学计量试剂和合成砌块的潜力仍是一个尚未充分探索但很有前景的领域。本综述旨在阐明NHCs及其N-杂环前体或衍生物在有机合成中这些鲜为人知的应用。此外，我们还讨论了如何利用NHCs独特的电子和空间性质来开发新的合成方法或构建有趣的有机骨架。通过突出这些新兴用途，我们希望鼓励对NHCs的非催化应用进行进一步研究，拓宽它们在合成化学中的范围和影响。
