Chakraborty Sukriyo, Barik Soumen, Biju Akkattu T
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Chem Soc Rev. 2025 Feb 3;54(3):1102-1124. doi: 10.1039/d4cs01179a.
N-Heterocyclic carbenes (NHCs) have been used as organocatalysts for a multitude of C-C and C-heteroatom bond-forming reactions. They enable diverse modalities of activating a wide range of structurally distinct substrate classes and allow access to electronically distinct intermediates. The easy tunability of the NHC scaffold contributes to its versatility. Recent years have witnessed a surge of interest in various organocatalytic reactions of NHCs, leading to the forays of NHC catalysis into the relatively newer domains such as reactions involving radical intermediates, atroposelective synthesis, umpolung of electrophiles other than aldehydes, and the use of NHCs as non-covalent templates for enantioinduction. This tutorial review provides an overview of various important structural features and reactivity modes of NHCs and delves deep into some frontiers of NHC-organocatalysis.
N-杂环卡宾（NHCs）已被用作多种碳-碳和碳-杂原子键形成反应的有机催化剂。它们能够以多种方式活化各种结构不同的底物类别，并能生成电子性质不同的中间体。NHC骨架易于调节，这有助于其多功能性。近年来，人们对NHCs的各种有机催化反应兴趣激增，促使NHC催化涉足相对较新的领域，如涉及自由基中间体的反应、阻转选择性合成、醛以外亲电试剂的极性翻转，以及将NHCs用作对映体诱导的非共价模板。本专题综述概述了NHCs的各种重要结构特征和反应模式，并深入探讨了NHC有机催化的一些前沿领域。
