613-90-1Relevant articles and documents
Selective Monohydrocyanation of Diimine using Potassium Hexacyanoferrate(II)-Benzoyl Chloride Reagent System as a Cyanide Source
Li, Zheng,Wen, Fei,Yang, Jingya
, p. 1849 - 1853 (2016)
The selective monohydrocyanation of diimines using potassium hexacyanoferrate(II)-benzoyl chloride reagent system as a cyanide source under catalyst-free condition is described. The advantages of this protocol are the non-toxic, non-volatile and inexpensive cyanide source, high yield, and simple work-up procedure. [Figure not available: see fulltext.]
CONVERSION OF 3-AZIDO-5-PHENYL-1,2,4-OXADIAZOLE INTO BENZOYL CYANIDE; A NEW THERMAL FRAGMENTATION
Choi, P.,Rees, C.W.,Smith, E.H.
, p. 121 - 124 (1982)
Flash vacuum pyrolysis of 3-azido-5-phenyl-1,2,4-oxadiazole gives benzoyl cyanide for which a mechanism involving the formation and fragmentation of N-benzoylpentaazafulvene is proposed.
Metal-Free Transformation of Sulfonyl Oxime Ethers with Amines to Oxime Ethers
Zhang, Jia-Yuan,Hu, Jinglin,Li, Xiao-Xuan,Tang, Wei-Ke,Feng, Yi-Si
, p. 12676 - 12682 (2021/09/18)
Sulfonyl oxime ethers undergo facile radical substitutions with various amines to yield the corresponding oxime ethers. An efficient arylation of sulfonyl oxime ethers was accomplished under ambient temperature and metal-free conditions, with a wide range of functional group tolerance. Mechanistic investigations indicate that a phenyl radical is involved in the catalytic cycle.
Copper-mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols
Dong, Jianyu,Chen, Xiuling,Ji, Fangyan,Liu, Lixin,Su, Lebin,Mo, Min,Tang, Jian-Sheng,Zhou, Yongbo
, (2020/10/20)
A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.
Thiocyanate radical mediated dehydration of aldoximes with visible light and air
Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
supporting information, p. 9701 - 9704 (2019/08/15)
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source
Lu, Hao,Li, Zheng
supporting information, p. 4474 - 4482 (2019/08/20)
Palladium-catalyzed one-pot four-component synthesis of β-cyano-α,β-unsaturated ketones by the reactions of aryl halides, calcium carbide, potassium hexacyanoferrate(II) and aroyl chlorides is described. The salient features of this protocol are the direct use of easy-to-handle acetylene source and eco-friendly cyanide source, wide scope of substrates with good functional group tolerance, and simple work-up procedure. (Figure presented.).
Reactions of 3-(Polyfluoroalkyl)propane-1,2,3-trione-2-oximes with Diaminoarenes
Boltacheva,Slepukhin,Pervova,Filyakova,Charushin
, p. 416 - 423 (2019/05/06)
Novel quinoxaline derivatives have been synthesized via the reaction of 3-trifhioromethyl-1,2,3-propanetrione-2-oximes with 1,2-diaminobenzene or 2,3-diaminonaphthalene: 2-trifluoromethyl-3-aroylquinoxaline and 2-trifluoromethyl-3-aroylbenzo[g]quinoxaline. Under similar conditions, 3-RF-1,2,3-propanetrione-2-oximes [RF = C3F7, H(CF2)4, C4F9, and C6F13] with the same diaminoarenes have given a mixture of the condensation and fragmentation products in different ratios. The structure of (4-methylphenyl)[3-(tri-fluoromethyl)benzo[g]quinoxalin-2-yl]methanone has been elucidated by means of X-ray diffraction analysis.
Aerobic oxidation of alcohols with air catalyzed by decacarbonyldimanganese
Meng, Shan-Shui,Lin, Li-Rong,Luo, Xiang,Lv, Hao-Jun,Zhao, Jun-Ling,Chan, Albert S. C.
supporting information, p. 6187 - 6193 (2019/11/20)
The oxidation of alcohols to carbonyl compounds using air as the terminal oxidant is highly desirable. As described in previous reports, the abstraction of α-H of the alcohol is the most important step, and it typically requires not only a metal catalyst but also complex ligands, co-catalysts and bases. Herein, we report a practical and efficient method for the oxidation of primary alcohols, secondary alcohols, 1,2-diols, 1,2-amino alcohols, and other α-functionalized alcohols using a commercially available catalyst, Mn2(CO)10, and no additives. Preliminary mechanistic studies indicated that an alkoxyl radical intermediate existed in our system, and a plausible mechanism consistent with the experimental results and literature was proposed.
A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp3)-H-Oxidation of Benzylic Nitriles
Eisele, Pascal,Bauder, Michael,Hsu, Shih-Fan,Plietker, Bernd
, p. 689 - 691 (2019/05/07)
A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru-catalyzed selective C?H-oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C?H-oxidation-Tischenko-rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.
Synthesis method of benzoyl cyanide
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Paragraph 0011; 0017; 0018; 0021, (2019/04/29)
The invention discloses a synthesis method of benzoyl cyanide. The method is characterized in that sodium cyanide and benzoyl chloride are taken as raw materials, the mixture of polyethylene glycol 600 and trioctylmethylammonium chloride is taken as a phase transferring catalyst, water or glycerol is taken as an auxiliary catalyst, the reaction with the benzoyl chloride is conducted at the temperature of 60 DEG C-110 DEG C, a benzoyl cyanide coarse product and a reaction bi-product are prepared after the reaction is conducted for 3-5 hours, and the coarse product is washed and separated to prepare a benzoyl cyanide fine product under the action of a solvent. The method has the advantages that the benzoyl cyanide is synthesized through a simple method, an alkaline chlorination method is adopted to perform treatment in order to reduce pollution and turn harm into benefit, and therefore cyanide is oxidized and destructed by active chlorine under strong alkaline conditions to generate atoxic sodium chloride; the solvent can be recycled, so that the synthesis method has the advantages of low pollution, high conversion, simple operation and the like.
