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Recent developments in electrosynthesis of nitriles and electrocatalytic cyanations
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作者 Haiyan Hu Shanxuan Wu +4 位作者 Fachao Yan Mohamed Makha Yuxia Sun Chen-Xia Du Yuehui Li 《Journal of Energy Chemistry》 SCIE EI CAS CSCD 2022年第7期542-575,I0014,共35页
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
关键词 Cyano compounds NITRILES cyanation ELECTROSYNTHESIS ELECTROCATALYSIS
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Anodic Cyanation of 1-(1-Methoxycarbonyl ethyl) piperidine
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作者 PingZHAO YingWuYIN 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第9期1043-1046,共4页
Aminonitriles were prepared efficiently from anodic cyanation of ?amino ester. The effect of different solvents and electrolytes was studied. The other byproducts were analyzed.
关键词 Aminonitriles 1-(1-methoxycarbonylethyl) piperidine anodic cyanation electrolysis.
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Decarboxylative cyanation and thiocyanation via catalytic electron donor-acceptor complex with copper catalysis
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作者 Hongping Zhao Xiaoxiang Xi +3 位作者 Tianbao Wu Zimin Chen Minyan Wang Weiming Yuan 《Science China Chemistry》 SCIE EI CAS CSCD 2024年第9期3019-3028,共10页
A new catalytic decarboxylative cyanation and thiocyanation via a synergistic Na I/Cu catalysis is developed.The photoexcited electron donor-acceptor complex by assembly of Na I,R3P,and N-acyloxy-phthalimide ester(NHP... A new catalytic decarboxylative cyanation and thiocyanation via a synergistic Na I/Cu catalysis is developed.The photoexcited electron donor-acceptor complex by assembly of Na I,R3P,and N-acyloxy-phthalimide ester(NHPI ester)triggers the generation of alkyl radical species,which then engages in Cu-catalyzed radical coupling process.Key to success of this dual catalytic transformation is the reliable charge transfer between I·and Cu(I).This dual catalytic platform can eliminate the use of expensive iridium-based photocatalyst or synthetically elaborate organic dyes.A series of primary,secondary,and tertiary alkyl nitriles and thiocyanates are easily synthesized.Moreover,an asymmetric decarboxylative cyanation by applying a chiral Cu catalyst is also developed to afford chiral nitriles in high enantioselectivity.The mechanistic details and the origin of the high enantioselectivity are further investigated by the mechanistic experiments and the density functional theory calculations. 展开更多
关键词 electron donor-acceptor catalysis copper catalysis cyanation THIOcyanation asymmetric synthesis
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Construction of remote cyano-substituted quaternary carbon centers via nickel-catalyzed migratory hydrocyanation of unconjugated dienes
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作者 Yidan Xing Rongrong Yu +2 位作者 Mingdong Jiao Ting Wang Xianjie Fang 《Science China Chemistry》 SCIE EI CAS CSCD 2024年第10期3397-3405,共9页
The transition-metal-catalyzed migratory functionalization has emerged as a robust protocol for the building of C–C bonds remote from the“initiation”position.However,a similar strategy for the construction of quate... The transition-metal-catalyzed migratory functionalization has emerged as a robust protocol for the building of C–C bonds remote from the“initiation”position.However,a similar strategy for the construction of quaternary carbon centers is still underdeveloped and only a limited number of reports exist.Herein,we report a nickel-catalyzed migratory hydrocyanation of unconjugated dienes to construct remote cyano-substituted quaternary carbon centers.This transformation features exceptional regioselectivity,mild reaction conditions,broad substrate scope and high yields.The synthetic utility of this method has been highlighted by a series of product derivatizations,and the potential of this transformation has been extended to synthesize TRPV1 antagonist and the key intermediate in the total synthesis of quebrachamine.Density functional theory(DFT)studies unveiled that the specific catalytic pocket assumed a significant role in the selective formation of cyano-substituted quaternary carbon centers. 展开更多
关键词 chain-walking regioselectivity remote cyanation quaternary carbon centers unconjugated dienes
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Copper-Mediated Selective Multiple Inert Chemical Bonds Cleavage for Cyanation of Indoles via Tandem Carbon and Nitrogen Atom Transfer
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作者 Shimin Xie Fangfang Cai +3 位作者 Lixin Liu Lebin Su Jianyu Dong Yongbo Zhou 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2024年第19期2299-2304,共6页
Comprehensive Summary The activation of inert chemical bonds is an exciting area of research in chemistry because it enables the direct utilization of readily available starting materials and promotes atom-and step-ec... Comprehensive Summary The activation of inert chemical bonds is an exciting area of research in chemistry because it enables the direct utilization of readily available starting materials and promotes atom-and step-economic synthesis.Undoubtedly,selectively activating and transforming multiple inert chemical bonds is an even more intriguing and demanding task in synthetic chemistry.However,due to its inherent complexity and extreme challenges,this endeavour is rarely accomplished.We report a copper-mediated complete cleavage and selective transformation of multiple inert chemical bonds of three easily available feedstocks,i.e.,a sp^(2)C—H bond in indoles,three sp^(3)C—H bonds and one C—N bond in a methyl carbon atom in TMEDA,and the C≡N triple bond in CH_(3)CN.This reaction proceeds via tandem carbon and nitrogen atom transfer,and allows for the direct and efficient cyanation of indoles,presenting a simple and direct alternative for synthesizing 3-cyanoindoles. 展开更多
关键词 Multiple inert chemical bonds Bond cleavage Carbon and nitrogen atom transfer Cleavage reactions Oxidation Copper cyanation IndoleSelectivity
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Indole cyanation via C-H bond activation under catalysis of Ru(Ⅲ)-exchanged NaY zeolite(RuY) as a recyclable catalyst 被引量:2
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作者 Alireza Khorshidi 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第8期903-906,共4页
Selective 3-cyanation of indoles was achieved under heterogeneous catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst, in combination with K4[Fe(CN)6] as a nontoxic, slow cyanide releasing ... Selective 3-cyanation of indoles was achieved under heterogeneous catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst, in combination with K4[Fe(CN)6] as a nontoxic, slow cyanide releasing agent. Under the aforementioned conditions, good yields of the desired products were obtained. 展开更多
关键词 cyanation INDOLE ZEOLITE HETEROGENEOUS CATALYSIS
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Photoredox Catalysis Unlocks the Nickel-Catalyzed Cyanation of Aryl Halides under Benign Conditions 被引量:1
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作者 Yue Jia Yi-Yin Liu +4 位作者 Liang-Qiu Lu Shi-Han Liu Hong-Bin Zhou Yu Lan Wen-Jing Xiao 《CCS Chemistry》 CAS 2022年第5期1577-1586,共10页
The transition-metal-catalyzed cyanations of aryl halides are among the most used methods for synthesizing aryl nitriles.Despite tremendous advances,cyanating an aryl halide in a facile and benign fashion has generall... The transition-metal-catalyzed cyanations of aryl halides are among the most used methods for synthesizing aryl nitriles.Despite tremendous advances,cyanating an aryl halide in a facile and benign fashion has generally been unsuccessful.The challenge in this significant transformation is the strong affinity of cyanide for metals,which hampers oxidative addition(OD)and reductive elimination(RE)making organometallic catalysis elusive.Herein,we demonstrate for the first time that photoredox-nickel-catalyzed cyanations of aryl halides are readily enabled by visible light,in which Ni(Ⅱ)species are transiently oxidized to Ni(Ⅲ)species,thereby facilitating subsequent cyanide transfer and RE.Using this dual catalysis strategy,we cyanated aryl and alkenyl halides at room temperature in a highly benign manner(30 examples,53-93% yield)by avoiding the use of air-sensitive ligands,Ni(0)precursors,and hypertoxic cyanation reagents,while also limiting excess metal waste.Computational studies were also used to help understand the present transformation. 展开更多
关键词 nickel catalysis photoredox catalysis visible light cyanation reaction aryl nitrile
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Enantioselective cyanation of benzylic C—H bonds via copper-catalyzed radical relay 被引量:1
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《Science Foundation in China》 CAS 2016年第4期31-31,共1页
With the support by the National Natural Science Foundation of China and the Chinese Academy of Sciences,the research team led by Prof.Liu Guosheng(刘国生)at Shanghai Institute of Organic Chemistry,Chinese Academy of ... With the support by the National Natural Science Foundation of China and the Chinese Academy of Sciences,the research team led by Prof.Liu Guosheng(刘国生)at Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,and Prof.Shannon Stahl at the University of Wisconsin-Madison,discovered a copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C—H bonds 展开更多
关键词 H bonds via copper-catalyzed radical relay Enantioselective cyanation of benzylic C
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Ligand-accelerated, branch-selective oxidative cyanation of alkenes
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作者 Jun Yang Huan Li +4 位作者 Jian Qin Fan Song Jian Zhang Feng-Ling Qing Lingling Chu 《Science Bulletin》 SCIE EI CAS CSCD 2018年第22期1479-1484,共6页
A ligand-accelerated, branch-selective oxidative cyanation of alkenes has been developed in the presence of catalytic Cu_2O.Both styrenes and aliphatic alkenes with directing groups are well tolerated in this inexpens... A ligand-accelerated, branch-selective oxidative cyanation of alkenes has been developed in the presence of catalytic Cu_2O.Both styrenes and aliphatic alkenes with directing groups are well tolerated in this inexpensive protocol.The mild condition allows for a good tolerance of functional groups, enabling facile access to a diverse array of simple and complex branched vinyl nitriles.The wide synthetic utility of this methodology has been further demonstrated via the efficient scaleup in both batch and continuous flow processes. 展开更多
关键词 Vinyl nitrile cyanation Branch-selective ALKENE Copper catalysis
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Direct oxidative C(sp^3)-H cyanation of secondary benzylic ethers
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作者 Zehua Wang Ying Mao +4 位作者 Honghao Guan Min Cao Jing Hua Lei Feng Lei Liu 《Chinese Chemical Letters》 SCIE CAS CSCD 2019年第6期1241-1243,共3页
Current studies on the oxidative C--H functionalization of benzylic ethers for C--C forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a ... Current studies on the oxidative C--H functionalization of benzylic ethers for C--C forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a practical and efficient oxidative C--H cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans, facilely furnishing a library of isochromans bearing α-aryl α-cyano substituent patterns for further diversification and bioactive small molecule identification. 展开更多
关键词 C-H FUNCTIONALIZATION cyanation Oxidation SECONDARY ETHER TERTIARY ETHER synthesis
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Cu2O-Mediated Room Temperature Cyanation of Aryl Boronic Acids/Esters and TMSCN
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作者 Yong Ye Yanhua Wang +1 位作者 Pengtang Liu Fushe Han 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2013年第1期27-30,共4页
A method for the efficient and reliable synthesis of aryl nitriles via the Cu20-catalyed cross-coupling of aryl boronic acids or esters and TMSCN is presented. A broad range of substrates decorated by electron-rich an... A method for the efficient and reliable synthesis of aryl nitriles via the Cu20-catalyed cross-coupling of aryl boronic acids or esters and TMSCN is presented. A broad range of substrates decorated by electron-rich and defi- cient, sterically very congested, and labile functionalities were tolerated. Moreover, the reaction can proceed under mild conditions at room temperature. These advantages paired with the use of cheap, readily available, and halo- gen-free Cu20 as catalysts make the protocol an appealing option for aryl cyanations. 展开更多
关键词 copper boronic acid boronic ester cyanation aryl nitrile
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Copper- and Silver-Mediated Cyanation of Aryl Iodides Using DDQ as Cyanide Source
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作者 Kui Zheng Peng Yu +2 位作者 Shuyou Chen Fen Chen Jiang Cheng 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2013年第4期449-452,共4页
A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved, provid- ing nitriles with good yields. This new approach represents a safe method leading to aryl nitriles.
关键词 COPPER SILVER cyanation aryl iodides DDQ
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Copper-Catalyzed Cyanations of Aromatic Bromides with Benzoyl Cyanide
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作者 Liang Wang Liang Pan +1 位作者 Qun Chen Mingyang He 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2014年第12期1221-1224,共4页
Aromatic nitriles were synthesized through copper-catalyzed cyanations of aromatic bromides using benzoyl cyanide as the cyanide source.A series of functional groups were tolerated under the reaction conditions to pro... Aromatic nitriles were synthesized through copper-catalyzed cyanations of aromatic bromides using benzoyl cyanide as the cyanide source.A series of functional groups were tolerated under the reaction conditions to provide the products in good yields.Moreover,this protocol avoids using of highly toxic alkali cyanides and expensive palladium catalysts. 展开更多
关键词 NITRILES aromatic bromides benzoyl cyanide copper-catalysis cyanation
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N-Heterocyclic Carbene-Catalysed Direct Synthesis of Cyano Esters via Cyanation-Esterification Reaction of a-Keto Esters
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作者 Jie Zhang Ying Wang Guangfen Du Cheng-Zhi Gu Bin Dai 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2015年第10期1211-1215,共5页
The cyanation-esterification reaction of a-keto esters catalysed by N-heterocyclic carbenes (NHCs) is developed Under the catalysis of 10 tool% 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, aromatic and alipha... The cyanation-esterification reaction of a-keto esters catalysed by N-heterocyclic carbenes (NHCs) is developed Under the catalysis of 10 tool% 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, aromatic and aliphatic a-keto esters reacted with ethyl cyanoformate or acetyl cyanide to produce the corresponding cyano esters with a tetra- substituted carbon center in high yields. 展开更多
关键词 N-heterocyclic carbene cyanation reaction cyano ester ethyl cyanoformate acetyl cyanide
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Environmentally benign and economic synthesis of covalent triazine-based frameworks 被引量:2
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作者 张玲 刘学 +2 位作者 杨瑞霞 黄年玉 邓伟侨 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2017年第3期583-588,共6页
Covalent triazine-based frameworks(CTFs) are important microporous materials with a wide range of applications.Here,we demonstrate an environmentally benign and economic synthetic pathway to CTFs.The monomers used f... Covalent triazine-based frameworks(CTFs) are important microporous materials with a wide range of applications.Here,we demonstrate an environmentally benign and economic synthetic pathway to CTFs.The monomers used for CTFs,aromatic nitriles,were obtained by cyanation using nontoxic potassium hexacyanoferrate(Ⅱ) in place of commonly used toxic cyanides.Then,the CTFs were synthesized by trimerization of the corresponding cyano monomers in molten zinc chloride.A series of CTFs was synthesized,and the highest Brunauer-Emmett-Teller surface area measured in this series was 2404 m^2/g.Among the synthesized CTFs,CTF_(DCP) exhibited excellent CO_2 adsorption properties,with a CO_2 uptake of 225 mg/g at 0℃. 展开更多
关键词 Covalent triazine-based framework Aryl bromide cyanation Potassium hexacyanoferrate(Ⅱ) Palladium acetate
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Improved Electrochemical Synthesis of Nitro-substituted 1-Aryl-2-pyrrolidinecarbonitriles
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作者 Wei LIU Yuan MA +1 位作者 Ying Wu YIN Yu Fen ZHAO 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第6期736-738,共3页
In this paper, we described an improved electrochemical method for synthesis of some 1-aryl-2-pyrrolidinecarbonitrile derivatives bearing an electron-withdrawing group (NO2). The electrochemical synthesis of titile ... In this paper, we described an improved electrochemical method for synthesis of some 1-aryl-2-pyrrolidinecarbonitrile derivatives bearing an electron-withdrawing group (NO2). The electrochemical synthesis of titile compounds has been successfully performed in an undivided cell in reasonable yields. 展开更多
关键词 Anodic cyanation NITRILE PYRROLIDINE electrochemistry.
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硅胶功能化的N-丙哌嗪固载钯纳米粒子作为有效的多相催化剂用于氰化反应(英文)
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作者 Khodabakhsh NIKNAM Abdollah DERIS Farhad PANAHI 《催化学报》 CSCD 北大核心 2013年第4期718-722,共5页
An efficient heterogeneous Pd catalytic system has been developed, based on immobilization of Pd nanoparticles (PNPs) on a silica-bonded N-propylpiperazine (SBNPP) substrate. The SBNPP substrate effectively stabilizes... An efficient heterogeneous Pd catalytic system has been developed, based on immobilization of Pd nanoparticles (PNPs) on a silica-bonded N-propylpiperazine (SBNPP) substrate. The SBNPP substrate effectively stabilizes the PNPs and improves their stability against aggregation. The catalytic activity of this catalyst was investigated in the cyanation of aryl halides with K4[Fe(CN)6 ] as the cyanide source. The catalyst could be recycled several times without appreciable loss of catalytic activity. 展开更多
关键词 Palladium nanoparticle Silica‐bonded N‐propylpiperazine cyanation reaction ARYL HALIDE
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Reactions with Aminobenzoic Acids via Diazonium Salts Open New Routes to Bio-Derived Aromatics
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作者 Anthony Farlow Jens Olaf Krömer 《International Journal of Organic Chemistry》 CAS 2016年第2期95-99,共5页
Aromatics have a broad application in our everyday life ranging from plastics, coatings and fibres, to food and pharmaceuticals. To date the bulk of these aromatics is derived from naphtha-based pet-rochemistry. Howev... Aromatics have a broad application in our everyday life ranging from plastics, coatings and fibres, to food and pharmaceuticals. To date the bulk of these aromatics is derived from naphtha-based pet-rochemistry. However, recent progress in the fermentative production of metabolites using renew-able resources and engineered microbes has enabled the production of bio-precursors, such as 4-amino benzoic acid (pABA) and 2-amino benzoic acid (oABA). In this work we explored the feasibility of Sandmeyer reactions for the conversion of pABA to terephthalic and oABA salicylic acid, providing two very important platform chemicals for the chemical and pharmaceutical industries. We could demonstrate that both acids can be obtained from the amino benzoic acids derived from the shikimate pathway in microbes and plants. Good conversions could be achieved using Sandmeyer reactions at mild conditions with biodegradable reagents and without organic solvents. 展开更多
关键词 Aminobenzoic Acid Terephthalic Acid Salycilic Acid Sandmeyer cyanations
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Morphological, mechanical and thermal properties of cyanate ester/benzoxazine resin composites reinforced by silane treated natural hemp fibers 被引量:5
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作者 Abdeldjalil Zegaoui Ruikun Ma +5 位作者 Abdul Qadeer Dayo Mehdi Derradji Jun Wang Wenben Liu Yile Xu Wan'an Cai 《Chinese Journal of Chemical Engineering》 SCIE EI CAS CSCD 2018年第5期1219-1228,共10页
This present study deals with the reinforcement of thermosetting resin blends composed of cyanate ester(CE) and benzoxazine(BOZ) resins with natural hemp fibers(NHFs). These NHFs were initially treated by using a sila... This present study deals with the reinforcement of thermosetting resin blends composed of cyanate ester(CE) and benzoxazine(BOZ) resins with natural hemp fibers(NHFs). These NHFs were initially treated by using a silane coupling agent(SCA) in order to chiefly enhance their distributions as well as adhesions within the CE/BOZ resin matrix,then incorporated with various weight amounts ranging from 5 wt% to 20 wt% with a regular interval of 5 wt%. The obtained results showed that at the maximum treated fiber loading(20 wt%), distinctive enhancements in the mechanical properties in terms of flexural strength and microhardness were obtained. Besides, the thermal stability and glass transition temperature(Tg) were appreciably enhanced and were higher than those of the pure CE/BOZ resin properties. With respect to the astonishing properties of the NHFs, these enhancements could be possibly due to the good dispersion and adhesion of the treated NHFs inside the CE/BOZ resin achieved upon using the SCA. Therefore,we believe herein that these renewable and cheap NHFs have considerable potential to be used as reinfocer materials for CE/BOZ resin composites to be used in various industrial sectors. 展开更多
关键词 Cyanate ester BENZOXAZINE Hemp fibers Thermal stabilities Mechanical properties
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A Study on the Properties of Resin Transfer Molding Cyanate Ester and Its T800 Grade Carbon Fiber Composites 被引量:5
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作者 Qiuren Ou Peijun Ji +1 位作者 Jun Xiao Ling Wu 《Fluid Dynamics & Materials Processing》 EI 2019年第1期27-37,共11页
The properties of resin transfer molding(RTM)cyanate ester and its T800 grade carbon fiber composites were studied with the rheometer,differential scanning calorimetry(DSC),FT-IR,dynamic mechanical analyzer(DMA),therm... The properties of resin transfer molding(RTM)cyanate ester and its T800 grade carbon fiber composites were studied with the rheometer,differential scanning calorimetry(DSC),FT-IR,dynamic mechanical analyzer(DMA),thermal gravimetric analysis(TGA),mechanical property testing,and scanning electron microscopy(SEM).The results showed that the temperature of cyanate ester suitable for RTM process was 70℃.Curing process of the resin was 130℃/2 h+160℃/2 h+200℃/2 h+220℃/4 h.Glass transition temperature and heat decomposition temperature of the cured resin are 289℃and 415℃,respectively.Mechanical properties of T800/RTM cyanate composites are 13.5%higher than that of T700/RTM cyanate composites and equal to that of T800/Prepreg cyanate composites.Tg of T800/RTM cyanate composites was proved to be 291℃.Fracture pattern of the composites was flat,which proved excellent interface properties between fiber and resin in this composite. 展开更多
关键词 RTM cyanate ester VISCOSITY glass transition temperature heat decomposition temperature mechanical properties
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