1197-33-7Relevant articles and documents
Iron and Phenol Co-Catalysis for Rapid Synthesis of Nitriles under Mild Conditions
Meng, Hong,Gao, Sen,Luo, Meiming,Zeng, Xiaoming
, p. 4617 - 4623 (2019/07/15)
A mild, scalable, high yielding, and rapid route to access diverse nitriles from aldehyde oxime esters enabled by iron(III) and phenol co-catalysis has been developed. The reaction was performed at room temperature to give nitriles in excellent yield within minutes. Mechanistic studies show that the reaction may proceed through a radical process in which benzoyl aldehyde oxime is not only a substrate, but also an ancillary ligand to support iron salt in the promotion of the transformation.
Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Sharif, Muhammad,Kalevaru, Narayana V.,Jagadeesh, Rajenahally V.
supporting information, p. 266 - 273 (2018/01/12)
The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.
Catalytic and oxidizing synthetic method of nitriles compound
-
Paragraph 0054, (2017/07/23)
The invention discloses a catalytic and oxidizing synthetic method of a nitriles compound. The catalytic and oxidizing synthetic method comprises the following steps: adding reaction substrate aldehyde, NH4OAc, alkaline additives, I2 and TBHP (tert-butyl hydroperoxide) into an ethanol solvent, facilitating the reaction for 3 to 17 h at 40 to 60 DEG C, adding a sodium thiosulfate solution into a reaction solution, stirring, extracting with diethyl ether, separating to obtain an organic layer, decompressing and steaming to remove the solvent, performing the column chromatography isolation, adopting a mixed solution of ethyl acetate/petroleum ether in a volume ratio of 1: 100 as an eluent, collecting an elution solution containing a target compound, and steaming to remove the solvent, thus obtaining the product nitriles, wherein a weight ratio of the reaction substrate aldehyde to the alkaline additives to NH4OAc to I2 to TBHP is 100: (100 to 120): (120 to 160): (2 to 3): (100 to 120). The synthetic method has the beneficial effects that the operation is simple and safe, and the reaction condition is relatively moderate; and the reaction substrate is wide in application range.
Aliphatic nitrile catalytic oxidation synthesis method
-
Paragraph 0037; 0038, (2016/10/17)
The invention discloses an aliphatic nitrile catalytic oxidation synthesis method. With aliphatic aldehyde serving as reaction substrate, 2, 2, 6, 6-tetramethylpiperidine-1-oxygen radical (TEMPO), alkali metal salt and tert-butyl nitrite (TBN) as catalysts, hexamethyl-disilazane (HMDS) as the nitrogen source and oxygen as an oxidizing agent, the reaction substrate is reacted in organic solvent at normal pressure at the temperature of 25-50 DEG C, and aftertreatment is performed after reaction to obtain the aliphatic nitrile. The method is easy and safe to operate, and environment cost is lowered.
Copper-catalyzed rearrangement of oximes into primary amides
Sharma, Sumeet K.,Bishopp, Simon D.,Liana Allen,Lawrence, Ruth,Bamford, Mark J.,Lapkin, Alexei A.,Plucinski, Pawel,Watson, Robert J.,Williams, Jonathan M.J.
supporting information; experimental part, p. 4252 - 4255 (2011/08/22)
The atom-efficient and cost-effective rearrangement of oximes into primary amides is catalyzed by simple copper salts. The use of homogeneous Cu(OAc) 2 (1-2 mol %) was found to be effective for this transformation at 80 °C. The reaction was successful with either conventional or microwave heating. CuO and CuO/ZnO on activated carbon provided a competent reuseable heterogeneous catalyst which could be used in a batch process or in flow. Copper salts are much cheaper than the precious metals previously used for this rearrangement, and the reaction conditions are milder than those reported.
A facile Zn-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from Baylis-Hillman adducts in water and its application
Das, Biswanath,Chowdhury, Nikhil,Banerjee, Joydeep,Majhi, Anjoy,Mahender, Gurram
, p. 358 - 359 (2007/10/03)
A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH 4C1 solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica (F). Copyright
An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis-Hillman adducts using NaBH4/CuCl 2·2H2O
Das, Biswanath,Banerjee, Joydeep,Majhi, Anjoy,Mahender, Gurram
, p. 9225 - 9227 (2007/10/03)
A convenient and facile stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been achieved by treatment of unactivated Baylis-Hillman adducts with NaBH4 in the presence of CuCl 2·2H2O at room temperature for 15 min.
Highly Convenient, One-Pot Synthesis of Nitriles from Aldehydes Using the NH2OH·HCl/NaI/MeCN System
Ballini, Roberto,Fiorini, Dennis,Palmieri, Alessandro
, p. 1841 - 1843 (2007/10/03)
Direct transformation of both aliphatic and aromatic aldehydes to the corresponding nitriles, can be easily performed by the reaction of an aldehyde with a slight excess of hydroxylamine hydrochloride, in refluxing acetonitrile and in the presence of 0.5 equivalents of sodium iodide as catalyst.
Zinc(II) promoted conversion of aryltriazenes to aryl iodides and aryl nitriles
Patrick, Timothy B.,Juehne, Thomas,Reeb, Elmer,Hennessy, Daniel
, p. 3553 - 3554 (2007/10/03)
Aryltriazenes react with zinc perchlorate/zinc cyanide to produces arylnitriles and react with zinc iodide to produce aryliodides. The reaction mechanism involves aryl radicals that have been trapped by addition to propenenitriles in a good preparative Meerwein arylation process.
