17104-67-5Relevant academic research and scientific papers
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, 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.
Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes
Chen, Hao,Mondal, Arup,Wedi, Philipp,Van Gemmeren, Manuel
, p. 1979 - 1984 (2019/02/19)
Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.
Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
Yu, Peng,Morandi, Bill
, p. 15693 - 15697 (2017/12/02)
We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.
Reductive activation of arenes 22. Reactions of the terephthalonitrile radical anion and dianion with α,ω-dibromoalkanes. New evidence for the charge transfer complex as a key intermediate in the reactions of the dianion
Panteleeva,Lukyanova,Pokrovsky,Shteingarts
, p. 1110 - 1118 (2008/09/18)
The major products of reactions of the terephthalonitrile radical anion with α,ω-dibromoalkanes Br(CH2)nBr (n = 3-5) were 4-(ω-bromoalkyl)benzonitriles. Analogous reactions of the terephthalonitrile dianion mainly yielded α,ω-bis(4-cyanophenyl) alkanes. Both transformations are convenient one-step routes to otherwise not easily accessible compounds that are valuable as versatile building blocks. The results of alkylation allow one to suggest that reactions of the dianion with intermediate 4-(ω-bromoalkyl)benzonitriles proceed more rapidly than those with the starting α,ω-dibromoalkanes. This was confirmed by competitive reactions of the dianion with 4-(ω-bromoalkyl)benzonitriles and the corresponding alkyl bromides. To explain such a ratio of the reaction rates, a mechanism was proposed for the reaction of the dianion with 4-(ω-bromoalkyl)benzonitriles. According to this mechanism, a charge transfer complex is a key reaction intermediate.
A PROCESS FOR THE PREPARATION OF 3-CYANO-1-NAPHTHOIC ACID AND SOME ANALOGUES THEREOF
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Page 23, (2010/02/05)
The present invention is related to a process for the preparation of 3-cyano-1-naphthoic acid and some analogues thereof of formula (1), the intermediate 1-halo-3-cyano naphthalene and some analogues thereof used in this process and a process for the preparation of said intermediate.
Nickel Catalysed Conversion of Phenol Triflates into Aromatic Nitriles and Acids
Chambers, Mark R. I.,Widdowson, David A.
, p. 1365 - 1366 (2007/10/02)
Phenols, as their trifluoromethanesulphonate (triflate) esters, are converted by potassium cyanide in the presence of catalytic tetrakistriphenylphosphinenickel(0) into the corresponding nitriles, thence to the carboxylic acids.
