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Indazolin-3-ylidenes (Indy*): easily accessible, sterically-hindered indazole-derived N-heterocyclic carbenes and their application in gold catalysis

https://doi.org/10.1039/D4DT00287C

Zhang, Jin; Liu, Ting; Zhang, Gaopeng; Cai, Jianglong; Wang, Yue; Tong, Jianbo; Ma, Yangmin; Szostak, Roman; Szostak, Michal (February 2024, Dalton Transactions)

We report novel sterically-hindered ligands with strong σ-donation from the C3-indazole carbene center and flexible N-substitution with a 2,6-bis(diphenylmethyl)aryl group that extends beyond the metal center in non-classical N-heterocyclic carbenes.
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Copper(I)–Thiazol-2-ylidenes: Highly Reactive N-Heterocyclic Carbenes for the Hydroboration of Terminal and Internal Alkynes. Ligand Development, Synthetic Utility, and Mechanistic Studies

https://doi.org/10.1021/acscatal.2c04668

Zhang, Jin; Li, Xue; Li, Tao; Zhang, Gaopeng; Wan, Kerou; Ma, Yangmin; Fang, Ran; Szostak, Roman; Szostak, Michal (December 2022, ACS Catalysis)

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An air-stable, well-defined palladium–BIAN–NHC chloro dimer: a fast-activating, highly efficient catalyst for cross-coupling

https://doi.org/10.1039/D2CC02253B

Zhang, Jin; Li, Tao; Li, Xue; Zhang, Gaopeng; Fang, Shuai; Yan, Wenxuan; Li, Xiangyang; Yang, Xiufang; Ma, Yangmin; Szostak, Michal (June 2022, Chemical Communications)

We report the synthesis, characterization and reactivity of an air-stable, well-defined acenaphthoimidazolylidene palladium–BIAN–NHC chloro dimer complex, [Pd(BIAN–IPr)(μ-Cl)Cl] 2 . This rapidly activating catalyst merges the reactive properties of palladium chloro dimers, [Pd(NHC)(μ-Cl)Cl] 2 , with the attractive structural features of the BIAN framework. [Pd(BIAN–IPr)(μ-Cl)Cl] 2 is the most reactive Pd( ii )–NHC precatalyst discovered to date undergoing fast activation under both an inert atmosphere and aerobic conditions. The catalyst features bulky-yet-flexible sterics that render the C–H substituents closer to the metal center in combination with rapid dissociation to monomers and strong σ-donor properties. [Pd(BIAN–IPr)(μ-Cl)Cl] 2 should be considered as a catalyst for reactions using well-defined Pd( ii )–NHCs.
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