Extracurricular laboratory: Synthetic route of 141556-42-5

Although many compounds look similar to this compound(141556-42-5)Reference of 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, numerous studies have shown that this compound(SMILES:CC1=CC(C)=CC(C)=C1[N+]2=[C-]N(C3=C(C)C=C(C)C=C3C)C=C2), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called NHC-stabilized copper(I) aryl complexes and their transmetalation reaction with aryl halides, published in 2020-07-15, which mentions a compound: 141556-42-5, Name is 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, Molecular C21H24N2, Reference of 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene.

The authors report herein the synthesis, spectroscopic and structural characterization of NHC-stabilized Cu aryl complexes (NHC = N-heterocyclic carbene) [Cu(NHC)(Ar)] 1-5, 7-22 with various aryl ligands (4-Me-C6H4, 4-MeO-C6H4, 2,4,6-Me3C6H2, C6F5, 4-CF3-C6H4, (3,5-(CF3)2C6H3), 2,3,5,6-Me4-C6H, 2,6-iPr2-C6H3, C6Me5) and NHCs (IiPr, ItBu, IMes, IPr). Three different synthetic routes were used to obtain these complexes: (i) reaction of a Cu(I) aryl complex with a free NHC; (ii) reaction of an NHC-stabilized Cu(I) chloride with a Grignard reagent, which is one important step in Kumada-Tamao-Corriu type cross-coupling reactions; and (iii) reaction of an NHC-stabilized Cu(I) alkoxide with an organoboronic ester, which represents an important step in Suzuki-Miyaura type cross-coupling reactions. The latter process was studied in detail by VT-NMR experiments using [Cu(IPr)(OtBu)] and 4-CF3-C6H4Bpin as an example, revealing the formation of an adduct (A) as a reaction intermediate. Also, the reactivity of the [Cu(NHC)(Ar)] complexes towards aryl halides was studied.

Although many compounds look similar to this compound(141556-42-5)Reference of 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, numerous studies have shown that this compound(SMILES:CC1=CC(C)=CC(C)=C1[N+]2=[C-]N(C3=C(C)C=C(C)C=C3C)C=C2), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles