121358-86-9Relevant articles and documents
Copper-catalyzed domino halide exchange-cyanation of aryl bromides
Zanon, Jacopo,Klapars, Artis,Buchwald, Stephen L.
, p. 2890 - 2891 (2003)
An efficient copper-catalyzed domino halogen exchange-cyanation procedure for aryl bromides was developed utilizing 10 mol % CuI, 20 mol % KI, 1.0 equiv of the inexpensive N,N′-dimethylethylenediamine as ligand, and 1.2 equiv of NaCN in toluene at 110 °C. The new method represents a significant improvement over the traditional Rosenmund-von Braun reaction: the reaction conditions are much milder, and the use of stoichiometric amounts of copper(I) cyanide and polar solvents is avoided; therefore the isolation and purification of the aromatic nitrile products is greatly simplified. In addition, the new method exhibits excellent functional group compatibility comparable to that of the analogous Pd-catalyzed cyanation methodology. Copyright
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
N-alkyl-cyanopyrazole synthetic method
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Paragraph 0032, (2018/11/22)
The invention discloses an N-alkyl-cyanopyrazole synthetic method which comprises the following step of by taking 1-alkyl-1H-pyrazole formaldehyde or a derivative thereof, ammonia water, sodium bromate and acetic acid as raw materials and water as a reaction solvent to obtain N-alkyl-cyanopyrazole . The synthetic method provided by the invention is simple in technology without using extremely toxic substances, convenient in synthesis, high in yield, convenient in purification of an obtained product and beneficial to large-scale industrial production.
