In 1991, American chemist Anthony J. Arduengo successfully isolated stable N-heterocyclic carbenes and characterized their single-crystal structures, breaking the long-standing cognition barrier that carbenes could not be stably captured. Since then, N-heterocyclic carbene (NHC) chemistry has entered a period of rapid development[1].

In the field of chiral ligands, Herrmann and Enders reported the pioneering asymmetric catalytic work of chiral NHC-metal complexes in 1996. They coordinated imidazolium carbenes bearing chiral phenethyl N-substituents with rhodium to realize asymmetric hydrosilylation of acetophenone, yet only a moderate enantioselectivity of 32% was achieved. This groundbreaking study verified that chiral NHCs could act as stereodirecting ligands, while simultaneously exposing core drawbacks of early systems: single structural types, low enantioselectivity, and uncontrollable conformational flexibility[2-3].

Over the subsequent two decades, researchers continuously optimized ligand backbone rigidity and chiral transmission pathways. Recently, the Shi group proposed an original design concept of "induced-fit catalysis" and developed sterically hindered flexible chiral NHC ligands including ANIPE and SIPE series. These ligands break the limitations of traditional rigid ligand frameworks and exhibit outstanding performance in a wide range of asymmetric transformations involving inert bond activation[4]. Meanwhile, the Fan Qinghua group developed a series of tunable C₁-symmetric chiral NHC ligands, greatly enriching the library of chiral NHC skeletons[5].

In catalytic applications, diverse high-efficiency chiral NHC ligands have been widely coordinated with transition metals such as Cu, Ni, Pd, Ru and Ir. They are applied to high-value asymmetric reactions, including asymmetric cross-coupling, conjugate addition, C(sp²)/C(sp³)–H functionalization, alkene borylation/hydrosilylation, and asymmetric olefin metathesis[6-8].

To facilitate related academic research, we newly launch a chiral N-heterocyclic carbene ligand kit containing 8 premium ligand structures, all of which have demonstrated remarkable catalytic activity and stereoselectivity in various organic transformations. Representative reaction applications are listed below:

Chiral NHC ligand (CAS: 2101989-97-1) coordinated with palladium constitutes an efficient catalytic system for asymmetric [3+2] cycloaddition of α-allene amides and vinyl epoxides. This one-step reaction constructs functionalized chiral tetrahydrofuran scaffolds bearing consecutive tertiary and quaternary stereocenters, and the exocyclic alkene moiety is available for further orthogonal functionalization[9].

Combining chiral NHC ligand (CAS: 1033618-49-3) with copper triflate delivers a robust catalytic platform for asymmetric conjugate addition of Grignard reagents to 3-substituted cyclohexenones, enabling facile construction of chiral quaternary carbon stereocenters in a single operation[10].

Zero-valent nickel complexed with chiral NHC ligand (CAS: 2101989-97-1) catalyzes the asymmetric reductive coupling of aldehydes and internal alkynes with high regioselectivity. The reaction generates chiral silyl allylic alcohols with sterically bulky alkyne-terminal adduct structures and simultaneously establishes secondary alcohol stereocenters[11].

Cat-Lab (Anhui) Co., Ltd. officially releases the exclusive chiral N-heterocyclic carbene ligand kit. Customized synthesis services for novel NHC precursors and free carbene ligands are available for global academic institutions and industrial R&D teams. We sincerely welcome worldwide inquiries and research cooperation.

[1] A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.[2] W. A. Herrmann, L. J. Gooßen, C. Köcher, G. R. J. Artus, Angew. Chem. 1996, 108, 2980.[3] D. Enders, H. Gielen, G. Raabe, J. Runsink, J. H. Teles, Chem. Ber. 1996, 129, 1483.[4] Z.-C. Wang, S.-L. Shi, Acc. Chem. Res. 2025, 58, 2157.[5] J. Han, Y.-M. He, Y. Pan, F. Li, D. Li, W. Hao, Q.-H. Fan, CCS Chem. 2023, 5, 2088.[6] V. César, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 2004, 33, 619.[7] D. Janssen-Müller, C. Schlepphorst, F. Glorius, Chem. Soc. Rev. 2017, 46, 4845.[8] C. Costabile, S. Pragliola, F. Grisi, Symmetry 2022, 14, 1615.[9] W.-Y. Wang, J.-Y. Wu, Q.-R. Liu, X.-Y. Liu, C.-H. Ding, X.-L. Hou, Org. Lett. 2018, 20, 4773.[10] Y. Matsumoto, K. Yamada, K. Tomioka, J. Org. Chem. 2008, 73, 4578.[11] H. Wang, G. Lu, G. J. Sormunen, H. A. Malik, P. Liu, J. Montgomery, J. Am. Che