623-00-7Relevant academic research and scientific papers
Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: V. Synthesis of 4-bromophthalonitrile
Bagirzade,Tagiev
, p. 1085 - 1090 (2014)
Oxidative ammonolysis of 4-bromo-o-xylene on a V-Sb-Bi-Zr/γ-Al 2O3 catalyst gives 74.82 mol % of 4-bromophthalonitrile at a high conversion of the starting xylene in a one-cycle process. The process with recirculation results in decreased number of by-products and contribution of deep oxidation and increased selectivity in 4-bromophthalonitrile up to 95.42-96.58%.
Dibromofluoromethylation of aryl Grignard reagents with dibromodifluoromethane in the presence of LiBr
Shiosaki, Masahiro,Inoue, Munenori
, p. 160 - 168 (2015)
The dibromofluoromethylation of aryl Grignard reagents bearing electron-withdrawing groups with dibromodifluoromethane (CF2Br2) proceeded in the presence of LiBr. The reaction gave the corresponding α,α-dibromo-α-fluorotoluene derivatives through halogen exchange reaction of intermediate difluorobenzyl anions.
Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: I. Transformations of 4-bromo-o-xylene and 4-bromo-o-tolunitrile
Bagirzade
, p. 1672 - 1676 (2010)
Kinetic laws of 4-bromo-phthalonitrile synthesis by vapor-phase oxidative ammonolisis of 4- bromo-o-xylene in the range of 633-69 K were studied. It was shown that formation of 4-bromophthalonitrile proceeds successively through 4-bromo-o-tolunitrile. Conversion rates of 4-bromo-o-xylene and 4-bromo-o- toluinitrile were found to be described by half-order equations on the corresponding components and not to depend on the oxygen and ammonia concentrations. Pleiades Publishing, Ltd., 2010.
Cyanation of arylboronic acids in aqueous solutions
Ma, Longle,Placzek, Michael S.,Hooker, Jacob M.,Vasdev, Neil,Liang, Steven H.
, p. 6597 - 6600 (2017)
A copper-mediated 11C-cyanation method employing arylboronic acids and [11C]HCN has been developed. This method was applied to the radiochemical synthesis of a wide range of aromatic 11C-nitriles in aqueous solutions. The use of readily accessible arylboronic acids as precursors makes this method complementary to the well-established 11C-cyanation methods that utilize aryl halide precursors.
Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4460 - 4467 (2022/03/15)
Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
Synthesis, Characterization, and Catalytic Study of Caffeine-Derived N-heterocyclic Carbene Palladium Complexes
Chen, Haiqun,Huynh, Han Vinh,Liu, Ziwei,Lu, Yuchen,Meng, Qi,Teng, Qiaoqiao,Yuan, Dan,Zhao, Yaru
, p. 161 - 168 (2022/02/07)
Homo- and heterodicarbene palladium complexes bearing caffeine-derived N-heterocyclic carbene ligands were synthesized and fully characterized by NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The superior acidity of the alkylated ca
Biomass chitosan-derived nitrogen-doped carbon modified with iron oxide for the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles
Wang, Wei David,Wang, Fushan,Chang, Youcai,Dong, Zhengping
, (2020/11/24)
Nitrogen-doped carbon catalysts have attracted increasing research attention due to several advantages for catalytic application. Herein, cost-effective, renewable biomass chitosan was used to prepare a N-doped carbon modified with iron oxide catalyst (Fe2O3@NC) for nitrile synthesis. The iron oxide nanoparticles were uniformly wrapped in the N-doped carbon matrix to prevent their aggregation and leaching. Fe2O3@NC-800, which was subjected to carbonization at 800 °C, exhibited excellent activity, selectivity, and stability in the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles. This study may provide a new method for the fabrication of an efficient and cost-effective catalyst system for synthesizing nitriles.
Revisiting the synthesis of aryl nitriles: a pivotal role of CAN
Saikia, Rakhee,Park, Kwihwan,Masuda, Hayato,Itoh, Miki,Yamada, Tsuyoshi,Sajiki, Hironao,Mahanta, Sanjeev P.,Thakur, Ashim J.
, p. 1344 - 1351 (2021/02/27)
Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN?leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.
Direct bromodeboronation of arylboronic acids with CuBr2 in water
Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei
supporting information, (2021/01/05)
An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.
SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution
Liao, Xudong,Zhou, Yi,Ai, Chengmei,Ye, Cuijiao,Chen, Guanghui,Yan, Zhaohua,Lin, Sen
supporting information, (2021/11/01)
A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.
