In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Monosubstituted, Anionic Imidazolyl Ligands from N-H NHC Precursors and Their Activity in Pd-Catalyzed Cross-Coupling Reactions, published in 2020-07-17, which mentions a compound: 1008-89-5, mainly applied to monosubstituted nitrogen heterocyclic carbene palladium complex preparation; aryl halide boronic acid Suzuki Miyaura Sonogashira coupling reaction, SDS of cas: 1008-89-5.
The treatment of several 2-diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N-H NHC-Pd complexes via insertion into the C-P bond is reported. Removal of the N-H proton in situ leads to anionic (X-type) or imidazolyl-Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki-Miyaura reactions. DFT-calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross-coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions.
Although many compounds look similar to this compound(1008-89-5)SDS of cas: 1008-89-5, numerous studies have shown that this compound(SMILES:C1(C2=CC=CC=C2)=NC=CC=C1), 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