91054-33-0Relevant academic research and scientific papers
A Serendipitous One-Pot Cyanation/Hydrolysis/Enamide Formation: Direct Access to 3-Methyleneisoindolin-1-ones
Banik, Trisha,Kaliappan, Krishna P.
, p. 628 - 633 (2020/12/09)
A direct, one-pot conversion of 2’-haloacetophenones to 3-methyleneisoindolin-1-one scaffolds using CuCN as the sole reagent without the need for moisture-free or anaerobic conditions is reported. This serendipitously discovered transformation with a broa
Synthesis of 2-Acetylbenzonitriles and Their Reactivity in Tandem Reactions with Carbon and Hetero Nucleophiles: Easy Access to 3,3-Disubstituted Isoindolinones
Di Mola, Antonia,Di Martino, Miriam,Capaccio, Vito,Pierri, Giovanni,Palombi, Laura,Tedesco, Consiglia,Massa, Antonio
, p. 1699 - 1708 (2018/04/24)
2-Acetylbenzonitriles have been conveniently synthesized by the oxidation of the respective 2-ethylbenzonitriles, combining in a one-pot procedure radical bromination and hydrolysis reactions. The obtained ketones reacted under very mild conditions with c
Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
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Paragraph 0043; 0045; 0139-0141, (2018/11/03)
The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
supporting information, p. 2118 - 2121 (2017/04/27)
A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
Microwave-assisted one-step synthesis of acetophenones via palladium-catalyzed regioselective arylation of vinyloxytrimethylsilane
Qian, Wangke,Zhang, Lei,Sun, Haifeng,Jiang, Hualiang,Liu, Hong
supporting information, p. 3231 - 3236 (2013/01/15)
The regiochemistry of the palladium-mediated arylation (Heck arylation) of enol ethers is sensitive to the structure of the enol ether, the arylating agent and the catalytic system. In this study, an effective and practical method was successfully developed for the synthesis of acetophenones with high regioselectivity under palladium-catalyzed conditions. A variety of acetophenones was readily prepared from aryl iodides in good to excellent yields under microwave irradiation in a single step. The key feature of our new protocol is the use of vinyloxytrimethylsilane as a highly regioselective acylation reagent. Copyright
Highly stereoselective chemoenzymatic synthesis of the 3 h -isobenzofuran skeleton. access to enantiopure 3-methylphthalides
Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
supporting information; experimental part, p. 1444 - 1447 (2012/06/01)
A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found to be the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.
Microwave-enhanced synthesis of aryl nitriles using dimeric orthopalladated complex of tribenzylamine and K4[Fe(CN)6]
Hajipour, Abdol Reza,Rafiee, Fatemeh,Ruoho, Arnold E.
experimental part, p. 526 - 529 (2012/02/01)
The activity of palladacycle [Pd{C6H4(CH 2N(CH2Ph)2)} (μ-Br)]2 complex was investigated in the synthesis of benzonitriles under both conventional and microwave irradiation conditions and their results were compared together. This complex is an efficient, stable, and non-sensitive to air and moisture catalyst for the cyanation reaction. The substituted benzonitriles were produced of various aryl halides in excellent yields and short reaction times using a catalytic amount of [Pd{C6H4(CH2N(CH 2Ph)2)} (μ-Br)]2 complex and K 4[Fe(CN)6] in DMF at 130 °C. In comparison to conventional heating conditions, the reactions under microwave irradiation gave higher yields in shorter reaction times.
Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst
Hajipour, Abdol-Reza,Abrisham, Fatemeh,Tavakoli, Ghazal
experimental part, p. 725 - 730 (2012/06/29)
A new dimeric ortho-palladated complex of 2-methoxyphenethylamine was synthesized and characterized and its application as a cyanation catalyst was investigated. The main advantages of this catalyst are its easy preparation, handling, stability, and moisture insensitivity. Thus, [Pd{C6H 3(CH2CH2NH2)-4-OMe-5-κ 2-C,N}(μ-Br)]2 showed excellent catalytic activity for the cyanation of aryl iodides and bromides with K4[Fe(CN) 6], in DMF in the presence of K2CO3 under microwave irradiation and conventional heating at 130 °C to give the desired cyanoarene products in good to high yields. The less reactive aryl chlorides also react with K4[Fe(CN)6] to give moderate yields of the aromatic nitriles. The effects of various parameters such as solvent, base, and amount of catalyst were studied. The reaction is suitable for a wide variety of substituted aryl halides with different electronic properties. Application of microwave irradiation improved the yields of the reactions and reduced the reaction times from hours to minutes. Graphical Abstract: Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst [Figure not available: see fulltext.]
Candida tenuis xylose reductase catalysed reduction of acetophenones: The effect of ring-substituents on catalytic efficiency
Vogl, Michael,Kratzer, Regina,Nidetzky, Bernd,Brecker, Lothar
experimental part, p. 5863 - 5870 (2011/09/30)
The catalytic efficiencies of Candida tenuis xylose reductase catalysed reductions of mono-substituted acetophenones are in reasonable correlation with the σ-Hammett coefficients of the substituted phenyl groups. Variations of the substrate transformation rates are hence mainly caused by mesomeric and inductive effects of the substituents, while differences in substrate binding have a secondary relevance. Some substrate 1H NMR chemical shifts and carbonyl IR absorption bands are in reasonable accordance with the catalytic activities and allow the estimation of the transformation rates with good accuracy. The resulting substituted (S)-1-phenyl ethanols are generated in very high enantiomeric excess.
An efficient palladium catalytic system for microwave assisted cyanation of aryl halides
Hajipour, Abdol R.,Karami, Kazem,Tavakoli, Ghazal,Pirisedigh, Azade
experimental part, p. 819 - 824 (2011/03/21)
Application of a new catalytic system for cyanation reaction of various aryl halides using K4[Fe(CN)6] as cyanating source was examined. The reactions were performed under microwave irradiation and results showed that application of this catalytic system and DMF at 130 °C minimized the reaction times from hours to minutes in good to excellent yields.
