A rapid and eco-friendly one-pot protocol for the synthesis of nitriles has been developed by treating various araldehydes bearing electron withdrawing as well as electron donating groups with hydroxylamine hydrochlor...A rapid and eco-friendly one-pot protocol for the synthesis of nitriles has been developed by treating various araldehydes bearing electron withdrawing as well as electron donating groups with hydroxylamine hydrochloride in the presence of non-toxic,non-corrosive and reusable zinc oxide（ZnO） as the catalyst under solvent-free microwave irradiation.The present approach offers the advantages of a clean reaction,simple methodology,employing readily available catalyst,short reaction duration（〈1 min）,high selectivity;and high yield（90-98%）.展开更多
A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoxime using supported sulphuric acid on melamine-formaldehyde resin （MFR） under solvent-free condition has been developed. A varie...A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoxime using supported sulphuric acid on melamine-formaldehyde resin （MFR） under solvent-free condition has been developed. A variety of aromatic and aliphatic aldoximes were converted to the corresponding nitriles. The resin was recovered and reused for subsequent reactions. ~ 2011 Ramin Rezaei. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.展开更多
Density, ρ, ultrasonic speed, u, and viscosity, η, of binary mixtures of 2-methyl-2-propanol (2M2P) with acetonitrile (AN), propionitrile (PN) and butyronitrile (BN) including those of pure liquids are measured over...Density, ρ, ultrasonic speed, u, and viscosity, η, of binary mixtures of 2-methyl-2-propanol (2M2P) with acetonitrile (AN), propionitrile (PN) and butyronitrile (BN) including those of pure liquids are measured over the entire composition range at temperatures 298.15, 303.15 and 308.15 K. From these experimental data, the excess available volume, E a V , excess free volume, E f V , excess isothermal compressibility, E T β , excess thermal expansion coefficient, E α , and excess internal pressure, E i π , are calculated. The variation of these properties with composition and temperature are discussed in terms of molecular interactions between unlike molecules of the mixtures. It is found that the values of E a V , E f V , E T β and E α are positive and those of E i π are negative for all the mixtures at each temperature studied, indicating the presence of weak interactions between 2M2P and AN/PN/BN molecules. The variations of E a V , E f V , E T β , E α and E i π values with composition indicate that the interactions in these mixtures follow the order: AN<PN<BN, i.e., the 2M2P-nitrile interaction decreases with the increase of alkyl chain length in these nitrile molecules. In addition, the theoretical ultrasonic velocity is calculated using the scaled particle theory and compared with the experimental values.展开更多
A simple,efficient,and general method has been developed for the synthesis ofα-amino nitriles.Oxalic acid as a BrФnsted acid promotes the addition of TMSCN to various imines（generated in situ）.
The intermolecular reductive coupling of nitrites with azobenzene induced by SmI2 was studied. Amidine derivatives were prepared in good yields under neutral and mild conditions.
A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is des...A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is described.展开更多
Indium(III) triflate, a trivalent indium reagent, was shown to be a highly-efficient catalyst for the conversion of primary amides to the corresponding nitriles. The successful reactions required 5 mol% of indium(III)...Indium(III) triflate, a trivalent indium reagent, was shown to be a highly-efficient catalyst for the conversion of primary amides to the corresponding nitriles. The successful reactions required 5 mol% of indium(III) triflate, and toluene was proved to be the most suitable solvent. Various amides were subjected to this method, and each produced the corresponding nitriles in excellent yields.展开更多
By screening the copper catalysts,ligands,and the reaction conditions,a simple CuCl/DMEDA/TEMPO catalyst system readily available from commercial sources is developed for a direct and selective synthesis of the useful...By screening the copper catalysts,ligands,and the reaction conditions,a simple CuCl/DMEDA/TEMPO catalyst system readily available from commercial sources is developed for a direct and selective synthesis of the useful nitriles by an aerobic oxidation reaction of primary amines using air as an advantageous oxidant under mild conditions.展开更多
Pentylpyridinium tribromide and aqueous ammonium acetate was used for the rapid oxidative conversion of benzyl alcohols, benzaldehydes and benzyl amines to the corresponding benzonitriles in good to excellent yields. ...Pentylpyridinium tribromide and aqueous ammonium acetate was used for the rapid oxidative conversion of benzyl alcohols, benzaldehydes and benzyl amines to the corresponding benzonitriles in good to excellent yields. This simple, mild and one-pot system provides easy workup and separation of the products.展开更多
A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCI/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses t...A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCI/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature, A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.展开更多
A continuous-flow synthesis of nitriles by Schmidt reaction has been developed.Using this procedure,a variety of aldehydes could be smoothly transformed into the desired nitriles in good to excellent yields.The mild r...A continuous-flow synthesis of nitriles by Schmidt reaction has been developed.Using this procedure,a variety of aldehydes could be smoothly transformed into the desired nitriles in good to excellent yields.The mild reaction conditions and the flowing reaction system greatly improved the safety and make the reaction easy to scale up.展开更多
Nitrile compounds are a class of high-value chemicals and versatile intermediates which can easily be transformed into a variety of useful products bearing functional groups such as carboxyl, carbamoyl, aminomethyl, k...Nitrile compounds are a class of high-value chemicals and versatile intermediates which can easily be transformed into a variety of useful products bearing functional groups such as carboxyl, carbamoyl, aminomethyl, ketyl and heterocyclic derivatives. Various thermal catalytic cyanation procedures have been devised and scaled up industrially while developing alternative methods are actively pursued. The access to these classes of molecules electrochemically offers greener alternatives to their preparation. The development of electrochemical synthesis of cyano-containing compounds under mild conditions with low energy consumption will imminently become indispensable approaches for industrial production of nitriles. The electrochemical cyanation presents many challenges from the toxicity of cyanide to the development of catalysts and the design of electrochemical cells. Electrochemical cyanation reaction offers promise to conveniently accessing nitriles but still requires efficient electro-catalysts, safe protocols and scale up considerations. This review discusses recent progress in the field of electrochemical synthesis of nitrile compounds placing emphasis on electro-synthetic and electro-catalytic mechanism aspects while making reference to original works to highlight the progress in this area.展开更多
The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene（DBU） in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yie...The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene（DBU） in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.展开更多
A simple and efficient method has been developed for the synthesis ofα-amino nitriles from aldehydes,amines and trimethylsilyl cyanide（Me_3SiCN） in the presence of a catalytic amount of cyanuric acid at room temper...A simple and efficient method has been developed for the synthesis ofα-amino nitriles from aldehydes,amines and trimethylsilyl cyanide（Me_3SiCN） in the presence of a catalytic amount of cyanuric acid at room temperature.展开更多
A new 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN using a copper and photoredox synergetic catalysis for producingα-amido allenyl nitriles is developed.Employing N-amidopyridin-1-ium sa...A new 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN using a copper and photoredox synergetic catalysis for producingα-amido allenyl nitriles is developed.Employing N-amidopyridin-1-ium salts as the amidyl radical precursors,the reaction enables the formation of two new bonds,one C(sp^(3))-N bond and one C(sp^(2))-C(sp)bond,in a single reaction step.This reaction represents a mild,general route to the construction of theα-amido allenyl nitrile architectures,which characterizes a broad scope,a good functional group compatibility and an excellent selectivity.展开更多
The Se-St bond in arylselenotrimethylsilane was reduced by samarium diiodide to produce samarium arylselenolate, which reacted with a,β-unsaturated esters or α,β-unsaturated nitriles to give β-selenoesters and β-...The Se-St bond in arylselenotrimethylsilane was reduced by samarium diiodide to produce samarium arylselenolate, which reacted with a,β-unsaturated esters or α,β-unsaturated nitriles to give β-selenoesters and β-selenonitriles, respectively.展开更多
The efficient dehydrosulfurization of thioamides to nitriles was carried out using indium(III) triflate as a catalyst. Based on the results of the initial study, the optimal reaction conditions required 5 mol% of indi...The efficient dehydrosulfurization of thioamides to nitriles was carried out using indium(III) triflate as a catalyst. Based on the results of the initial study, the optimal reaction conditions required 5 mol% of indium(III) triflate with toluene as the practical solvent. Various thioamides were successfully converted to nitriles in high yields.展开更多
文摘A rapid and eco-friendly one-pot protocol for the synthesis of nitriles has been developed by treating various araldehydes bearing electron withdrawing as well as electron donating groups with hydroxylamine hydrochloride in the presence of non-toxic,non-corrosive and reusable zinc oxide（ZnO） as the catalyst under solvent-free microwave irradiation.The present approach offers the advantages of a clean reaction,simple methodology,employing readily available catalyst,short reaction duration（〈1 min）,high selectivity;and high yield（90-98%）.
文摘A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoxime using supported sulphuric acid on melamine-formaldehyde resin （MFR） under solvent-free condition has been developed. A variety of aromatic and aliphatic aldoximes were converted to the corresponding nitriles. The resin was recovered and reused for subsequent reactions. ~ 2011 Ramin Rezaei. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
文摘Density, ρ, ultrasonic speed, u, and viscosity, η, of binary mixtures of 2-methyl-2-propanol (2M2P) with acetonitrile (AN), propionitrile (PN) and butyronitrile (BN) including those of pure liquids are measured over the entire composition range at temperatures 298.15, 303.15 and 308.15 K. From these experimental data, the excess available volume, E a V , excess free volume, E f V , excess isothermal compressibility, E T β , excess thermal expansion coefficient, E α , and excess internal pressure, E i π , are calculated. The variation of these properties with composition and temperature are discussed in terms of molecular interactions between unlike molecules of the mixtures. It is found that the values of E a V , E f V , E T β and E α are positive and those of E i π are negative for all the mixtures at each temperature studied, indicating the presence of weak interactions between 2M2P and AN/PN/BN molecules. The variations of E a V , E f V , E T β , E α and E i π values with composition indicate that the interactions in these mixtures follow the order: AN<PN<BN, i.e., the 2M2P-nitrile interaction decreases with the increase of alkyl chain length in these nitrile molecules. In addition, the theoretical ultrasonic velocity is calculated using the scaled particle theory and compared with the experimental values.
基金supported by the Islamic Azad University,Ayatollah Amoli Branch
文摘A simple,efficient,and general method has been developed for the synthesis ofα-amino nitriles.Oxalic acid as a BrФnsted acid promotes the addition of TMSCN to various imines（generated in situ）.
文摘The intermolecular reductive coupling of nitrites with azobenzene induced by SmI2 was studied. Amidine derivatives were prepared in good yields under neutral and mild conditions.
文摘A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is described.
文摘Indium(III) triflate, a trivalent indium reagent, was shown to be a highly-efficient catalyst for the conversion of primary amides to the corresponding nitriles. The successful reactions required 5 mol% of indium(III) triflate, and toluene was proved to be the most suitable solvent. Various amides were subjected to this method, and each produced the corresponding nitriles in excellent yields.
基金NNSFC(Nos.51502174,21672163)ZJNSF(No.LR14B020002)+2 种基金Postdoctoral Science Foundation of China(Nos.2015 M582401,2016M592520)for financial supportpartially supported by Science and Technology Project of Shenzhen(Nos.JCYJ20150324141711616,JCYJ20150626090504916)Science and Technology Planning Project of Guangdong Province(No.2016B050501005)
文摘By screening the copper catalysts,ligands,and the reaction conditions,a simple CuCl/DMEDA/TEMPO catalyst system readily available from commercial sources is developed for a direct and selective synthesis of the useful nitriles by an aerobic oxidation reaction of primary amines using air as an advantageous oxidant under mild conditions.
文摘Pentylpyridinium tribromide and aqueous ammonium acetate was used for the rapid oxidative conversion of benzyl alcohols, benzaldehydes and benzyl amines to the corresponding benzonitriles in good to excellent yields. This simple, mild and one-pot system provides easy workup and separation of the products.
文摘A mild and efficient methodology for the direct oxidative synthesis of nitriles from easily available alcohols and aqueous ammonia by employing CuCI/DABCO/4-HO-TEMPO as the catalysts is described. This protocol uses the air as a green oxidant and aqueous ammonia as the nitrogen source at room temperature, A variety of aryl, heterocyclic and allylic alcohols are smoothly converted into the corresponding nitriles in good to excellent yields.
基金the National Natural Science Foundation of China(No.21877005)for financial support
文摘A continuous-flow synthesis of nitriles by Schmidt reaction has been developed.Using this procedure,a variety of aldehydes could be smoothly transformed into the desired nitriles in good to excellent yields.The mild reaction conditions and the flowing reaction system greatly improved the safety and make the reaction easy to scale up.
基金supports from the National Natural Science Foundation of China(22022204,21633013)the Natural Science Foundation of Jiangsu Province(BK20180248).
文摘Nitrile compounds are a class of high-value chemicals and versatile intermediates which can easily be transformed into a variety of useful products bearing functional groups such as carboxyl, carbamoyl, aminomethyl, ketyl and heterocyclic derivatives. Various thermal catalytic cyanation procedures have been devised and scaled up industrially while developing alternative methods are actively pursued. The access to these classes of molecules electrochemically offers greener alternatives to their preparation. The development of electrochemical synthesis of cyano-containing compounds under mild conditions with low energy consumption will imminently become indispensable approaches for industrial production of nitriles. The electrochemical cyanation presents many challenges from the toxicity of cyanide to the development of catalysts and the design of electrochemical cells. Electrochemical cyanation reaction offers promise to conveniently accessing nitriles but still requires efficient electro-catalysts, safe protocols and scale up considerations. This review discusses recent progress in the field of electrochemical synthesis of nitrile compounds placing emphasis on electro-synthetic and electro-catalytic mechanism aspects while making reference to original works to highlight the progress in this area.
基金the National Natural Science Foundation of China (No. 21362022) for financial support
文摘The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene（DBU） in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.
文摘A simple and efficient method has been developed for the synthesis ofα-amino nitriles from aldehydes,amines and trimethylsilyl cyanide（Me_3SiCN） in the presence of a catalytic amount of cyanuric acid at room temperature.
基金the National Natural Science Foundation of China(No.22271245)for the financial supportthe Yantai“Double Hundred Plan”the Talent Induction Program for Youth Innovation Teams in Colleges and Universities of Shan-dong Province。
文摘A new 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN using a copper and photoredox synergetic catalysis for producingα-amido allenyl nitriles is developed.Employing N-amidopyridin-1-ium salts as the amidyl radical precursors,the reaction enables the formation of two new bonds,one C(sp^(3))-N bond and one C(sp^(2))-C(sp)bond,in a single reaction step.This reaction represents a mild,general route to the construction of theα-amido allenyl nitrile architectures,which characterizes a broad scope,a good functional group compatibility and an excellent selectivity.
文摘The Se-St bond in arylselenotrimethylsilane was reduced by samarium diiodide to produce samarium arylselenolate, which reacted with a,β-unsaturated esters or α,β-unsaturated nitriles to give β-selenoesters and β-selenonitriles, respectively.
文摘The efficient dehydrosulfurization of thioamides to nitriles was carried out using indium(III) triflate as a catalyst. Based on the results of the initial study, the optimal reaction conditions required 5 mol% of indium(III) triflate with toluene as the practical solvent. Various thioamides were successfully converted to nitriles in high yields.
