In 2022,Miyakoshi, Takeru; Niggli, Nadja E.; Baudoin, Olivier published an article in Angewandte Chemie, International Edition. The title of the article was 《Remote Construction of N-Heterocycles via 1,4-Palladium Shift-Mediated Double C-H Activation》.Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride The author mentioned the following in the article:
In the past years, Pd0-catalyzed C(sp3)-H activation provided efficient and step-economical methods to synthesize carbo- and heterocycles via direct C(sp2)-C(sp3) bond formation. Herein, a 1,4-Pd shift allows access to N-heterocycles which are difficult to build via a direct reaction. It is shown that o-bromo-N-methylanilines undergo a 1,4-Pd shift at the N-Me group, followed by intramol. trapping by C(sp2)-H or C(sp3)-H activation at another nitrogen substituent and remote C-C bond formation to generate biol. relevant isoindolines and β-lactams. The product selectivity is influenced by the employed ligand, with NHCs favoring the product of remote C-C coupling against products arising from direct C-C coupling and N-demethylation. The results came from multiple reactions, including the reaction of 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride)
1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem