Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past decades, the conversion reactions of acetonitrile as a building block have become one of the most-attractive fields in organic synthesis. Especially in the field of electrochemical conversions involving acetonitrile, due to its good conductivity and environmentally friendly features, it has become a powerful and compelling tool to afford nitrogen-containing compounds or nitrile-containing compounds. In this review, we mainly discuss the research progress involving acetonitrile in the past five years, covering both conventional synthesis methods and electrochemical synthesis. Besides, a detailed discussion of the substrate scope and mechanistic pathways is provided.
17 February 2021 in The Journal of Organic Chemistry
An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range of substituted 2-aminobenzyl alcohols and (hetero)aryl or alkyl benzamides and nitriles were well compatible to afford various quinazolines in excellent yields. Merits of this new strategy are the high atom-economy, mild reaction conditions, and simple operation, and the methodology is suitable for a variety of substrates.
A base-promoted amidation of 1-aryl-2,2,2-trifluoroethanones with aminesviaHaller–Bauer reaction has been developed. This reaction directly transforms aryl trifluoroethanone into amides without the use of stoichiometric chemical oxidants or transition-metal catalysts.
27 October 2022 in Beilstein Journal of Organic Chemistry
The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access the aryl/heteroaryl quinolones in suitable amounts. In addition, the antibacterial and antifungal activities of the synthesized quinolines were evaluated in vitro, and the experimental results showed that the antibacterial activities of compounds 3ab, 3ad, and 3ah against Gram-positive bacteria and compound 3ck against C. albicans were better than the reference drug norfloxacin.
A novel protocol facilitated by Na2SO3 that enhances the efficiency of palladium-catalyzed Heck coupling and the homo-coupling reactions of arylhydrazines. This innovative method enables the effective construction of a diverse array of cinnamate derivatives and biphenyl compounds. Notably, these transformative reactions proceed smoothly at room temperature, leveraging the activation of C-N bonds. This technique not only streamlines the synthesis process but also expands our understanding and expertise in the realm of coupling reactions.