50789-45-2Relevant academic research and scientific papers
Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation
Gates, Bruce C.,Guan, Erjia,Meng, Xiangju,Wang, Chengtao,Wang, Hai,Wang, Liang,Wang, Sai,Xiao, Feng-Shou,Xu, Dongyang,Xu, Hua,Yang, Bo,Zhang, Jian
, p. 6299 - 6308 (2020/07/21)
There is a strong incentive for environmentally benign and sustainable production of organic nitriles to avoid the use of toxic cyanides. Here we report that manganese oxide nanorod-supported single-site Ru catalysts are active, selective, and stable for oxidative cyanation of various alcohols to give the corresponding nitriles with molecular oxygen and ammonia as the reactants. The very low amount of Ru (0.1 wt %) with atomic dispersion boosts the catalytic performance of manganese oxides. Experimental and theoretical results show how the Ru sites enhance the ammonia resistance of the catalyst, bolstering its performance in alcohol dehydrogenation and oxygen activation, the key steps in the oxidative cyanation. This investigation demonstrates the high efficiency of a single-site Ru catalyst for nitrile production.
Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
Fang, Wan-Yin,Qin, Hua-Li
, p. 5803 - 5812 (2019/05/14)
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
Ullmann diaryl ether synthesis catalyzed by copper (I)/pyridine-functionalized silane
Zhang, Baohua,Shi, Lanxiang,Guo, Ruixia,Liu, Sijie
, p. 930 - 932 (2016/07/06)
Ullmann-type diaryl ether synthesis was performed under mild conditions in DMF/K2CO3using a pyridinefunctionalized silane as a ligand. The productswere obtained in good yields. This method tolerates a variety of functional groups and is effective in the synthesis of hindered diaryl ethers and heteroaryl ethers.
Copper-catalyzed synthesis of nitriles by aerobic oxidative reaction of alcohols and ammonium formate
Yadav, Dilip Kumar T.,Bhanage, Bhalchandra M.
, p. 5106 - 5110 (2013/11/06)
An efficient methodology has been developed for the synthesis of nitriles through an aerobic oxidative reaction of alcohols and ammonium formate with copper as a homogeneous catalyst under a normal air atmosphere and solvent-free conditions. This protocol uses the air as a green oxidant and ammonium formate as the nitrogen source. A wide range of substrates were well tolerated in the reaction that gave water as a byproduct. A facile protocol, which uses copper as an effective homogeneous catalyst, has been developed for the oxidative synthesis of nitriles from alcohols and ammonium formate. This system uses air as a green oxidant and produces water as an environmentally benign side product. Copyright
A novel oxidative transformation of alcohols to nitriles: An efficient utility of azides as a nitrogen source
Rokade, Balaji V.,Malekar, Sanjeev K.,Prabhu, Kandikere Ramaiah
supporting information; experimental part, p. 5506 - 5508 (2012/07/03)
An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H 2O.
Metal-free arylation of oxygen nucleophiles with diaryliodonium salts
Jalalian, Nazli,Petersen, Tue B.,Olofsson, Berit
supporting information, p. 14140 - 14149,10 (2012/12/12)
Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright
Chemoselective Schmidt reaction mediated by triflic acid: Selective synthesis of nitriles from aldehydes
Rokade, Balaji V.,Prabhu, Kandikere Ramaiah
experimental part, p. 5364 - 5370 (2012/09/07)
An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction, is not observed in this reaction. Besides these advantages, the salient feature of this reaction is that it exhibits a remarkable chemoselectivity, as acid and ketone functionalities are well tolerated under the reaction conditions. The reaction is easily scalable, high yielding, and nearly instantaneous.
Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts
Jalalian, Nazli,Ishikawa, Eloisa E.,Silva, Luiz F.,Olofsson, Berit
supporting information; experimental part, p. 1552 - 1555 (2011/04/26)
A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky ortho-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, racemization-prone amino acid derivatives, and heteroaromatics are also tolerated. The methodology is expected to be of high utility in the synthesis of complex molecules and in the pharmaceutical industry.
CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
supporting information; experimental part, p. 7951 - 7954 (2010/01/16)
(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
