- Synthesis of Triazidochlorosilane (TACS). A NovelSilicon Mediated one pot Conversion of Aldehyde to Nitriles
-
Synthesis, structure elucidation of triazidochlorosilane (TACS) and a novel conversion of aldehydes to nitriles in one pot reaction on treatment with TACS (SiCl4-NaN3 in Situ) reagent in acetonitrile are described.
- Elmorsy, Saad S.,El-Ahi, Abdel-Aziz S.,Soliman, Hanan,Amer, Fathy A.
-
-
Read Online
- Kinetics and Mechanism of Oxygen Transfer in the Reaction of p-Cyano-N,N-dimethylaniline N-Oxide with Metalloporphyrin Salts. 5. The Influence of Imidazole Ligation of (meso-Tetrakis(2,6-dimethylphenyl)porphinato)manganese(III) Chloride on the Rates of Oxygen Transfer from N-Oxide to...
-
Equilibrium constants for mono- and bisligation of imidazole (ImH) with (meso-tetrakis(2,6-dimethylphenyl)porphinato)manganese(III) chloride ((Me8TPP)MnIIICl) have been determined so that the concentrations (dry CH2Cl2) of the three species (Me8TPP)MnIIICl, III(ImH)>Cl, and III(ImH)2>Cl may be calculated at different ImH concentrations.The equilibrium constants for ligation of the one and two imidazoles are K1 = 245 M-1 and β2 = 1.80 x 105 M-2.The reaction of p-cyano-N,N-dimethylaniline N-oxide (NO) with the manganese(III) porphyrin (under the pseudo-first-order conditions of i >> IIICl>i and in the presence and absence of ImH) is first order in both NO and manganese(III) porphyrin, and the rate-controlling step involves oxygen transfer with formation of higher valent manganese-oxo porphyrin species plus p-cyano-N,N-dimethylaniline (DA).From the dependence of the pseudo-first-order rate constants (kobsd) upon i, and a knowledge of the equilibrium constants for imidazole ligation there has been calculated the second-order-rate constants for the kinetic terms k1IIICl>, k2III(ImH)>Cl>, and k3III(ImH)2>Cl>.Comparison of the second-order rate constants (k1 = 3.4 X 10-2 M-1 s-1, k2 = 5.53 M-1 S-1, and k3 = 7.32 X 10-2 M-1 s-1) establishes that ligation by one imidazole increases the rate of reaction of the manganese(III)porphyrin with NO by ca. 166-fold.Bis-imidazole ligated species are blocked to reaction with NO.The higher valent manganese-oxo porphyrin species formed from the reaction of NO with III(ImH)>Cl has been shown to be the principal epoxidizing agent from the dependence of the percentage yield of epoxide upon the concentration of ImH in reactions with cis-cyclooctene using constant initial concentrations of (Me8TPP)MnIIICl and NO.Epoxidation reactions are not rate controlling, and epoxide is formed in competitive processes that involve the reaction of higher valent manganese-oxo porphyrin species with DA (and its oxidation products) and alkene.With exception of the sterically hindered trans-β-methylstyrene, the percentage yield of epoxide at 1.0 M alkene is essentially independent of the type of alkene.Increase in the concentration of alkene and the 1e- oxidizable 2,4,6-tri-tert-butylphenol fails to trap all higher valent manganese-oxo porphyrin species.This result is interpreted as being due to the initial formation of an intimate pair of oxo species and DA with competition between dissociation of DA and oxo species and oxidation of DA within the intimate pair.Epoxidation of alkene by the oxo species occurs after the latter dissociates from the intimate pair.
- Wong, Wah-Hun,Ostovic, Drazen,Bruice, Thomas C.
-
-
Read Online
- Laser flash photolysis study of the photoinduced oxidation of 4-(dimethylamino)benzonitrile (DMABN)
-
Aromatic amines are aquatic contaminants for which phototransformation in surface waters can be induced by excited triplet states of dissolved organic matter (3DOM*). The first reaction step is assumed to consist of a one-electron oxidation process of the amine to produce its radical cation. In this paper, we present laser flash photolysis investigations aimed at characterizing the photoinduced, aqueous phase one-electron oxidation of 4-(dimethylamino)benzonitrile (DMABN) as a representative of this contaminant class. The production of the radical cation of DMABN (DMABN+) after direct photoexcitation of DMABN at 266 nm was confirmed in accord with previous experimental results. Moreover, DMABN+ was shown to be produced from the reactions of several excited triplet photosensitizers (carbonyl compounds) with DMABN. Second-order rate constants for the quenching of the excited triplet states by DMABN were determined to fall in the range of 3 × 107-5 × 109 M?1 s?1, and their variation was interpreted in terms of electron transfer theory using a Rehm-Weller relationship. The decay kinetics of DMABN+ in the presence of oxygen was dominated by a second-order component attributed to its reaction with the superoxide radical anion (O2?). The first-order rate constant for the transformation of DMABN+ leading to photodegradation of DMABN was estimated not to exceed ≈5 × 103 s?1
- Leresche, Frank,Ludvíková, Lucie,Heger, Dominik,Klán, Petr,Von Gunten, Urs,Canonica, Silvio
-
-
Read Online
- Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues
-
The use of Pd(DPEPhos)Cl2 (P26) as a catalyst for the formation of benzonitriles and their heterocyclic analogues provides excellent complementarity to existing catalysts, allowing highly electron-deficient heterocyclic aryl halides to be effic
- Richardson, Jeffery,Mutton, Simon P.
-
-
Read Online
- Kinetics and Mechanisms of Oxygen Transfer in the Reaction of p-Cyano-N,N-Dimethylaniline N-Oxide with Metalloporphyrin Salts. 3. Catalysis by iron(III) Chloride
-
Decomposition of p-cyano-N,N-dimethylaniline N-oxide (NO) catalyzed by iron(III) chloride ((Cl8TPP)FeIIICl) yields as products p-cyano-N,N-dimethylaniline (DA), p-cyano-N-methylaniline (MA), and formaldehyde (CH2Cl2 solvent, 25 deg C, N2 atmosphere).Intermediate in the reaction are mono and bis NO complexes (Cl8TPP(Cl)FeIIINO and Cl8TPP(NO)FeIIINO, respectively).Oxygen transfer from the complexed NO species to the iron porphyrin is rate-limiting and provides the higher valent iron(IV) salts (IVO>+. and IVO>+.) and DA.The observed kinetics for reactions involving 10-100 turnovers of catalyst dictate that the catalyst is saturated in the formation of Cl8TPP(Cl)FeIIINO and that formation of Cl8TPP(NO)FeIIINO is unfavorable.The two iron(IV)-oxo porphyrin ?-cation radical species are converted back to the iron(III) porphyrin catalytic moieties by oxidation of DA -> MA + CH2O and oxidation of CH2O.Addition of 2,4,6-tri-tert-butylphenol (TBPH), 2,3-dimethyl-2-butene (TME), and cyclohexene results in the formation of TBP. and the respective epoxides, thus inhibiting the oxidation of DA and CH2O.The kinetics of the overall reaction and formation of each product may be simulated by employing the reactions of Scheme II and eq l-r, and from the simulations, the rates and equilibria, leading to the formation of the two iron(IV)-oxo porphyrin ?-cation radical species may be determined as can minimal rate constants for the oxidations of DA, CH2O, and TBPH and the epoxidation of TME and cyclohexene.The results obtained herein with the electron-deficient porphyrin, (Cl8TPP)Fe(III)Cl, are discussed and compared to those obtained previously when employing (TPP)FeIIICl as the catalyst.
- Dicken, C. Michael,Woon, T. C.,Bruice, Thomas C.
-
-
Read Online
- FeCl3 mediated one-pot route to nitriles
-
A new and convenient protocol for the transformation of aldehydes into nitriles using hydroxylamine hydrochloride by iron III chloride is presented. The protocol offers a very simple, cost efficient, and environmentally benign procedure with good to excellent yield of nitrile.
- Ghosh, Pranab,Subba, Raju
-
-
Read Online
- The Kinetics and Mechanisms of Oxygen Transfer in the Reaction of p-Cyano-N,N-dimethylaniline N-Oxide with Metalloporphyrin Salts. 4. Catalysis by meso-(Tetrakis(2,6-dimethylphenyl)porphinato)iron(III) Chloride
-
meso-(Tetrakis(2,6-dimethylphenyl)porphinato)iron(III) chloride ((Me8TPP)Fe(III)Cl) is a catalyst for the conversion of p-cyano-N,N-dimethylaniline N-oxide (NO) to p-cyano-N,N-dimethylaniline (DA), p-cyano-N-methylaniline (MA), p-cyano-N-formyl-N-methylaniline (FA), p-cyanoaniline (A), N,N'-dimethyl-N,N'-bis(p-cyanophenyl)hydrazine (H), N,N'-bis(p-cyanophenyl)-N-methylmethylenediamine (MD), and CH2O.All evidence supports these reactions to occur by equilibrium ligation of NO to iron(III) porphyrin followed by rate-detrmining oxygen transfer to yields as intermediate products DA and the iron(IV)-oxo porphyrin ?-cation radical.Stepwise oxidation of DA by the higher valent iron-oxo porphyrin species is responsible for the formation of the other products (i.e., DA-->-->FA, DA-->MA-->A, 2MA-->MD, and 2MA-->H).The oxidation potentials of (Me8TPP)Fe(III)OCH3 are comparable to those of the unsubstituted meso-(tetraphenylporphinato)iron(III) methoxide ((TPP)Fe(III)OCH3).The following results are, therfore, not surprising: (i) The second-order rate constant (kakb/k-a) for reaction of (Me8TPP)Fe(III)Cl with NO is but 3.3-fold smaller than in the case of the reaction of NO with (TPP)Fe(III)Cl; (ii) the percentage yields of products (DA, 53percent; MA, 24percent; A, 3percent; FA, 8percent; H, 7percent; MD, 5percent) are comparable to when (TPP)Fe(III)Cl is employed; and (iii) oxidation and epoxydation of added substrates are not rate-determining.Of considerable interest is the finding that epoxidation reactions using NO with (Me8TPP)Fe(III)Cl occur in much higher yield (80percent to 100percent) than when (TPP)Fe(III)Cl is used as the catalyst.
- Woon, T. C.,Dicken, C. Michael,Bruice, Thomas C.
-
-
Read Online
- Dimethylanilinic N-Oxides and Their Oxygen Surrogacy Role in the Formation of a Putative High-Valent Copper-Oxygen Species
-
The reaction of p-cyano-N,N-dimethylaniline N-oxide, an O-atom donor, with different copper(I) complexes (at room temperature and in acetone) indicates the formation via O-atom transfer of a high-valent copper oxyl species, CuII-O?, a putative key intermediate in the catalytic cycle of copper-containing monooxygenases. The formation of p-cyano-N-hydroxymethyl-N-methylaniline and p-cyano-N-methylaniline as the main products of the reaction highlight the capability of this species to hydroxylate strong C-H bonds (bond dissociation energy ～90 kcal/mol). A plausible mechanism for the reactivity of this catalytic system is proposed.
- Diaz, Daniel E.,Bhadra, Mayukh,Karlin, Kenneth D.
-
-
Read Online
- Microwave activation in organic synthesis: Natural Indian clay, EPIC(R) EPZG(R) and EPZ10(R) as novel heterogenous catalysts for rapid synthesis of nitriles from aldoximes in absence of solvent
-
The Conversion of aldoximes into nitriles was carried out in the absence of solvent under microwave irradiation using environmentally-friendly catalysts like natural kaolinitic clay, EPIC(R) EPZG(R) and EPZ10(R). Acceleration of reaction rate, simple work-up and formation of clean products are salient features of this method.
- Bandgar,Sadavarte,Sabu
-
-
Read Online
- Convenient conversion of aldoximes into nitriles with N-chlorosuccinimide and pyridine
-
Benzaldehyde oximes substituted with electron-donating groups are dehydrated to the corresponding benzonitriles by N-chlorosuccinimide/pyridine in acetonitrile. Benzaldehyde oxime itself and alkanal oximes afford the corresponding aldehydes. Thieme Stuttgart.
- Gucma, Miroslaw,Golebiewski, W. Marek
-
-
Read Online
- Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
-
Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.
- Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi
-
p. 4460 - 4467
(2022/03/15)
-
- Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate
-
The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration.
- Nonnhoff, Jannis,Gr?ger, Harald
-
-
- H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile
-
Abstract: One-pot condensation of pyrazole-4-aldehydes and hydroxylamine hydrochloride to form the corresponding oxime using formic acid as a medium and further dehydration of oxime using a catalytic amount of orthophosphoric acid to afford novel pyrazole-4-carbonitrile. This protocol serves as an ortho-phosphoric acid-catalyzed one-pot conversion of aldehyde to nitrile. Most remarkable features of this method are metal-free, cost-effective, atom efficiency with excellent yield (98–99%). This process will serve as a robust and scalable tool for the synthesis of valuable and versatile precursor (nitriles). This precursor will pave the way for the synthesis of various medicinally important valuable compounds. Graphic abstract: [Figure not available: see fulltext.].
- Choudhare, Tukaram S,Netankar, Prashant D,Shirsath, Sagar E,Wagare, Devendra S
-
-
- Efficient nitriding reagent and application thereof
-
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
- -
-
Paragraph 0219-0222
(2021/03/31)
-
- Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst
-
Trichloroacetonitrile has been found to be an efficient dehydrating agent for a range of aldoximes including aromatic and heterocyclic aldoxime yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction.
- Ma, Xiaoyun,Liu, Dan,Chen, Zhengjian
-
p. 3261 - 3266
(2021/06/30)
-
- Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion
-
Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu2O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.
- Liu, Wenbo,Tang, Peichen,Zheng, Yi,Ren, Yun-Lai,Tian, Xinzhe,An, Wankai,Zheng, Xianfu,Guo, Yinggang,Shen, Zhenpeng
-
p. 3509 - 3513
(2021/10/04)
-
- Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis
-
A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.
- De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio
-
-
- Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
-
We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.
- Zhang, Yanmeng,Zhang, He,Gao, Ke
-
p. 8282 - 8286
(2021/10/25)
-
- CO2-tuned highly selective reduction of formamides to the corresponding methylamines
-
We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.
- Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei
-
supporting information
p. 7534 - 7538
(2021/10/12)
-
- Nickel-Catalyzed Cyanation of Aryl Thioethers
-
A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.
- Delcaillau, Tristan,Woenckhaus-Alvarez, Adrian,Morandi, Bill
-
supporting information
p. 7018 - 7022
(2021/09/13)
-
- Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst
-
A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.
- Iizumi, Keiichiro,Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
-
supporting information
p. 1555 - 1559
(2020/11/10)
-
- Nickel-Catalyzed Amination of Aryl Chlorides with Amides
-
A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.
- Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao
-
supporting information
p. 687 - 691
(2021/01/09)
-
- CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source
-
Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.
- Ren, Yun-Lai,Shen, Zhenpeng,Tian, Xinzhe,Xing, Ai-Ping,Zhao, Zhe
-
-
- Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)
-
The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)
- -
-
Paragraph 0058; 0059
(2020/09/12)
-
- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
-
The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
-
supporting information
p. 281 - 285
(2020/01/28)
-
- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
-
A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
- Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
-
p. 17288 - 17292
(2020/05/18)
-
- An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions
-
Abstract: A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.
- Uludag, N.
-
p. 1640 - 1645
(2020/10/22)
-
- Palladium-Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source
-
A new source of “CN” employing formamide and cyanuric chloride is introduced for the cyanation reactions. The treatment of formamide and 2,4,6-trichloro-1,3,5-triazine (TCT; cyanuric chloride) afforded an efficient cyanating agent which it can be used as a nontoxic, readily available, and non-expensive reagent in the cyanation transformations. In this study, palladium-catalyzed cyanation of aryl halides was successfully accomplished using this new “CN” source in high yields.
- Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
-
p. 2699 - 2707
(2020/04/08)
-
- Continuous-flow synthesis of nitriles from aldehydes via Schmidt reaction
-
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.
- Zhan, Wei,Tong, Meng,Ji, Ling,Zhang, Han,Ge, Zemei,Wang, Xin,Li, Runtao
-
p. 973 - 976
(2019/01/29)
-
- Catalytic oxidative conversion of aldehydes into nitriles using NH3·H2O/FeCl2/NaI/Na2S2O8: A practical approach to febuxostat
-
A novel approach to convert aldehydes into nitriles using NH3·H2O/FeCl2/NaI/Na2S2O8 has been developed. Both alkyl and aryl nitriles were obtained in good to excellent yields. Electron-withdrawing and electron-donating groups, such as fluoro, chloro, bromo, nitro, ester, cyano, trifluoromethyl and alkoxy were tolerated. Notably, febuxostat and its intermediate, ethyl 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylate, were obtained in excellent yields.
- Chen, Han,Sun, Sijia,Xi, Haoying,Hu, Kaifang,Zhang, Ning,Qu, Jingping,Zhou, Yuhan
-
supporting information
p. 1434 - 1436
(2019/05/01)
-
- Uniform silver nanoparticles on tunable porous N-doped carbon nanospheres for aerobic oxidative synthesis of aryl nitriles from benzylic alcohols
-
Tunable N-doped carbon nanospheres from sucrose as carbon source and Tris(2-aminoethyl)amine (TAEA) as nitrogen source by a simple and easily reproducible method were prepared. It was demonstrated that the tunable N-doping of carbon spheres could be realized by altering the ratio of TAEA in the raw materials. The content of doped nitrogen, surface area, pore volume and pore size of carbon nanospheres were increased with the increasing of TAEA amount in the hydrothermal process. Prepared N-doped carbon nanospheres act as solid ligand for anchoring of Ag NPs which generated via chemical reduction of Ag ions. Benzylic alcohols and aldehydes were converted into the aryl nitriles by using Ag/N-CS-1 nanospheres as the catalyst and O2 as the oxidant, efficiently. This catalyst was stable and could use for 6 successful runs.
- Hashemi, Alireza Nemati,Eshghi, Hossein,Lamei, Kamran
-
-
- Method for preparing nitrile
-
The invention provides a method for preparing nitrile. Aldoxime carboxylic ester is used as a reactant to prepare a nitrile compound. The aldoxime carboxylic ester can be completely converted into corresponding nitrile under common catalysis of ferric salt and phenol within a few minutes. The method for preparing the nitrile has the advantages of gentle reaction conditions, simple and easy-to-getused reagents, cheap and environment-friendly catalyst, wide substrate application range, simple operation, rapid reaction and the like.
- -
-
Paragraph 0015
(2019/06/13)
-
- A carboxamide is the cyanogen source of aromatic nitrile to the preparation method of the (by machine translation)
-
The invention discloses a method for preparing aromatic nitrile, is under the action of the nickel catalyst, in order to carboxamide is the cyanogen source, and with various substituents haloarene coupled reactions, preparing aromatic nitrile. The reaction temperature is 100 - 160 °C, the reaction time is 6 - 24 hours. It overcomes the traditional aromatic nitrile of the synthesis method operation of complex steps, requires the use of a toxic, more expensive, functionalization of the cyanogen source as the reaction raw material and the like. Compared with the traditional method, this method is simple to use cheap, green non-toxic of the formamide is cyano sources; without the need of external dehydrating agent, formamide in the nickel catalyst of the catalytic dehydration at the same time, with a nickel catalyst in coordination with the halogenated aromatic hydrocyanation, more economic, high-efficiency, environmental protection; at the same time the method exhibits good substrate universality, to air, moisture, light are not sensitive, high yield, product separation and purification is simple, with wide application. (by machine translation)
- -
-
Paragraph 0015; 0016; 0017; 0018-0024; 0116; 0117-0119
(2019/05/08)
-
- Method for preparing important chemicals by using lignin as methyl sources
-
The invention relates to preparation of important chemical products by using methoxyl groups in lignin. According to a method, methyl provided by the lignin reacts with carbon monoxide and water underthe catalysis effects of catalysts to obtain acetic acid; reaction is performed with aminated compounds to obtain N-methylation products. The methoxyl groups in the lignin are used for preparing important chemical products for the first time; an important and continuous production path is provided for the preparation of various important chemical products.
- -
-
Paragraph 0097; 0098; 0120-0124
(2019/06/12)
-
- Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
-
Various aromatic nitriles could be obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions.
- Uchida, Ko,Togo, Hideo
-
-
- Synergistic catalysis of Cu+/Cu0 for efficient and selective N-methylation of nitroarenes with para-formaldehyde
-
In this paper, an inexpensive heterogeneous copper nanoparticles catalyst derived from CuAl-layered double hydroxide via an in situ topotactic transformation process was developed. Cu nanoparticles with uniform size were homogeneously dispersed on amorphous Al2O3 with strong metal-support interaction. Characterization results reveals that the Cu0 and Cu+ were simultaneously formed with Cu+ species as the dominant sites on the surface during the reduction process. The resultant catalyst Cu/Al2O3 demonstrates high catalytic activity, selectivity and durability for the reductive N-methylation of easily available nitroarenes in a cost-efficient, environmentally friendly and cascade manner. A broad spectrum of nitroarenes could be efficiently N-methylated to their corresponding N,N-dimethyl amines with good compatibility of various functional groups. The protocol is also applicable for the late-stage functionalization of biologically and pharmaceutically active nitro molecules. A structure-function relationship discloses that Cu0 and Cu+ sites on the surface pronouncedly boosts the reaction efficiency in a synergistic manner, in which Cu0 could facilitate H2 production and N-methylation of anilines, while Cu+ is considerably more active and participates in the overall process of the selective N-methylation of nitroarenes. Moreover, the catalyst also showed a strong stability and could be easily separated for successive reuses without an appreciable loss in activity and selectivity.
- Dong, Xiaosu,Wang, Zhaozhan,Yuan, Youzhu,Yang, Yong
-
p. 304 - 313
(2019/07/02)
-
- Iron and Phenol Co-Catalysis for Rapid Synthesis of Nitriles under Mild Conditions
-
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.
- Meng, Hong,Gao, Sen,Luo, Meiming,Zeng, Xiaoming
-
p. 4617 - 4623
(2019/07/15)
-
- Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles
-
Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides starting from the corresponding thioureas and of thiocyanates from dithiocarbamates.
- Gopi, Elumalai,Gravel, Edmond,Doris, Eric
-
supporting information
p. 4043 - 4045
(2019/06/24)
-
- Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions
-
The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.
- Yang, Luo,Liu, Yu-Ting,Park, Yoonsu,Park, Sung-Woo,Chang, Sukbok
-
p. 3360 - 3365
(2019/03/26)
-
- Selective utilization of methoxy groups in lignin for: N -methylation reaction of anilines
-
The utilization of lignin as a feedstock to produce valuable chemicals is of great importance. However, it is a great challenge to produce pure chemicals because of the complex structure of lignin. The selective utilization of specific groups on lignin molecules offers the possibility of preparing chemicals with high selectivity, but this strategy has not attracted attention. In this work, we propose a protocol to produce methyl-substituted amines by the selective reaction of the methoxy groups of lignin and aniline compounds. It was found that LiI in the ionic liquid 1-hexyl-3-methylimidazolium tetrafluoroborate could catalyze the reaction efficiently and the selectivity to the N-methylation product could be as high as 98%. Moreover, the lignin was not depolymerized in the reaction. As it was rich in hydroxyl groups, the residual material left over after the reaction was used as an efficient co-catalyst for the cycloaddition of epoxy propane with CO2, using KI as the catalyst.
- Mei, Qingqing,Shen, Xiaojun,Liu, Huizhen,Liu, Hangyu,Xiang, Junfeng,Han, Buxing
-
p. 1082 - 1088
(2019/02/03)
-
- Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine
-
We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage.
- Ueda, Yohei,Tsujimoto, Nagataka,Yurino, Taiga,Tsurugi, Hayato,Mashima, Kazushi
-
p. 994 - 999
(2019/02/03)
-
- Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis
-
The construction of N-methyl amine moieties is an important reaction that has found numerous applications. Development of new methylation agents that are more environmentally benign than classical agents, such as iodomethane and methyl sulfate, is still highly desirable. Herein, we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis. The present protocol operates under transition-metal-free and air-tolerant conditions. Both the catalyst, K2HPO4, and the reductant, polymethylhydrosiloxane (PMHS), are cheap and easily separable from the crude reaction product mixture. Mechanistic investigations suggest that the reaction occur through the formation of an acetal intermediate followed by the C–N bond formation.
- Huang, Yan,Deng, Wei,Lin, Bo-Lin
-
supporting information
(2019/05/29)
-
- Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS): An efficient catalyst for cyanation reaction in aqueous media
-
Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS) were found to be an efficient heterogeneous catalyst in the cyanation reaction of aryl halides in aqueous media. This catalyst system is containing palladium nanoparticles with a size of ～7 nm. Moreover, the CD-PU-NS support formed microsphere-shaped structures with a size of ～100–200 nm. The TEM images show that Pd nanoparticles were formed in near spherical shape morphology and were immobilized in the structure of the CD-PU-NS support. Under our optimized reaction conditions, aryl cyanides were obtained in high yields in the presence of the Pd-CD-PU-NS catalyst. Our results demonstrated that the Pd-CD-PU-NS catalyst is highly effective in the cyanation reaction in aqueous media. Furthermore, the catalyst could be simply extracted from the reaction mixture, providing an efficient methodology for the synthesis of aryl cyanides. The Pd-CD-PU-NS catalyst could be recycled four times with almost consistent catalytic efficiency.
- Khajeh Dangolani, Soheila,Sharifat, Sara,Panahi, Farhad,Khalafi-Nezhad, Ali
-
supporting information
p. 256 - 265
(2019/06/07)
-
- UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source
-
We demonstrate the first metal-organic framework (MOF) that catalyzes N-methylation of amines using 1 atm CO2 and phenylsilane under ambient conditions. Compared with its homogeneous analog, the incorporation of N-heterocyclic carbene (NHC) into the MOF provides more efficient catalysis with improved reaction kinetics, turnover numbers and recyclability. Moreover, the metalated NHC functionalized MOF achieves direct N-methylation of amines bearing carboxylate moieties, which are common building blocks in pharmaceutical chemistry.
- Zhang, Xu,Jiang, Yilin,Fei, Honghan
-
supporting information
p. 11928 - 11931
(2019/10/11)
-
- Cu(OAc)2/malononitrile/water: A simple reaction system for synthesis of aromatic nitriles from aldoximes
-
A simple method for the preparation of nitriles in moderate to good yield has been achieved by treatment of aromatic and heterocyclic aldoximes with malononitrile in water at reflux in the presence of copper acetate as catalyst. Arylaldoximes with an electron-donating group showed the highest reactivity, their conversion being achievable at room temperature.
- Ma, Xiaoyun,He, Daqin,Chen, Zhengjian
-
p. 595 - 597
(2018/12/13)
-
- Pd/Mn Bimetallic Relay Catalysis for Aerobic Aldoxime Dehydration to Nitriles
-
A Pd/Mn bimetal system was found to be an effective catalyst for dehydration of aldoximes to the useful nitriles under mild aerobic conditions. Different to the known metal-catalyzed aldoxime dehydration reactions, this reaction very possibly proceeded via an alternative mechanism of Pd/Mn bimetal relay catalysis involving a Mn-catalyzed aerobic oxidation of aldoximes to nitrile oxides by air and a Pd-catalyzed oxygen transfer from the nitrile oxides to the solvent acetonitrile. This method tolerates a variety of substrates including sterically bulky ones and also the natural product derivative. (Figure presented.).
- Zhang, Dongliang,Huang, Yaping,Zhang, Erlei,Yi, Rong,Chen, Chao,Yu, Lei,Xu, Qing
-
supporting information
p. 784 - 790
(2018/01/04)
-
- Magnetically recoverable lanthanum hydroxide as an efficient catalyst for Aerobic Oxidative Conversions of primary alcohols to the nitriles
-
Herein we report a novel magnetically recoverable lanthanum hydroxide nanoparticles for oxidative synthesis of nitriles directly from corresponding alcohols with ammonia as nitrogen source. The procedure for the preparation and characterization of La(OH)3/Fe3O4 magnetic nanoparticles were investigated and the scope and generality of the method was explored for a series of structurally diverse primary alcohols with electron-donating and electron-withdrawing groups. The best result was observed when 5?mol% of La with respect to the benzyl alcohol was used at reflux condition under O2 atmosphere. The La(OH)3/Fe3O4 magnetic nanoparticles could be easily isolated from the reaction mixture with an external magnet and reused at least 5 times without significant loss in activity.
- Ziaee, Fariborz,Gholizadeh, Mostafa,Seyedi, Seyed Mohammad
-
-
- An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
-
An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
- Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
-
p. 6958 - 6966
(2018/10/02)
-
- Cyaniding method for preparing nitrile compound
-
The invention provides a cyaniding method for preparing a nitrile compound. Organic halide or pseudohalide, CO2 and NH3 which are low in price and are easily obtained and a reducing agent react, a selective cyaniding reaction is conducted in the presence of a transition metal catalyst, and the target product namely organic the nitrile compound is obtained. According to the cyaniding method for preparing the nitrile compound, a new reaction route is used, through a CO2 and NH3 reaction of metal catalysis, dehalogenation cyaniding or quasi halide cyaniding of halide or pseudohalide is directly achieved through a one-pot method, the problem is solved that a traditional cyanation reaction needs equivalent toxic cyanide, a new direct and convenient method for preparing isotope-labeled nitrile compounds is provided at the same time, and the method can be applied to medicine, tracing, biology and medicine research and development.
- -
-
Paragraph 0228-0130
(2018/05/30)
-
- Catalytic Cyanation Using CO2 and NH3
-
Li and co-workers describe the catalytic cyanation of organic halides with CO2 and NH3. In the presence of Cu2O/DABCO as the catalyst, a variety of aromatic bromides and iodides were transformed to the desired nitrile products with broad functional-group tolerance. Both 13C- and/or 15N-labeled nitriles were obtained conveniently with appropriately isotope-labeled CO2 and NH3. Construction of functionalized chemical compounds from small molecules in a highly selective and efficient manner is crucial for sustainable development. The chemical-based manufacturing sector of the future should aim to produce chemicals from very simple and abundant resources, just as nature uses CO2 and N2 to generate sugars, amino acids, and so forth. In practice, however, the utilization of CO2 for the generation of industrial products, such as drugs and related intermediates, still remains a major challenge. Here, we describe the facile cyanide-free production of high-value nitriles with CO2 and NH3 as the sole sources of carbon and nitrogen, respectively. This practical and catalytic methodology provides a unique strategy for the utilization of small molecules for sustainable and cost-effective applications. Selective cyanation of aryl halides was achieved with CO2 and NH3 as the only sources of carbon and nitrogen, respectively. In the presence of Cu catalysts under low pressure (3 atm), a variety of aromatic iodides and bromides were transformed to the desired nitrile products without the use of toxic metal cyanides. Notably, olefins, esters, amides, alcohols, and amino groups were tolerated. Mechanistic studies suggest that Cu(III)-aryl insertion by isocyanate intermediates is involved. [13C,15N]-labeled nitriles were conveniently accessible from the respective isotope-labeled CO2 and NH3 via this methodology.
- Wang, Hua,Dong, Yanan,Zheng, Chaonan,Sandoval, Christian A.,Wang, Xue,Makha, Mohamed,Li, Yuehui
-
supporting information
p. 2883 - 2893
(2019/01/05)
-
- Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)2: A Route to Aryl Nitriles
-
A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C-O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.
- Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
-
supporting information
p. 2753 - 2756
(2018/05/22)
-
- 1,4-Dioxane-Tuned Catalyst-Free Methylation of Amines by CO2 and NaBH4
-
A catalyst-free reductive functionalization of CO2 with amines and NaBH4 was developed. The N-methylation of amines was carried out with CO2 as a C1 building block and 1,4-dioxane as the solvent. Notably, the six-electron reduction of CO2 to form the methyl group occurred simultaneously with formation of the C?N bond to give the N-methylated amine.
- Guo, Zhiqiang,Zhang, Bo,Wei, Xuehong,Xi, Chanjuan
-
p. 2296 - 2299
(2018/07/31)
-
- Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions
-
A one-pot protocol for the assembly of diversely functionalized tetrahydro-, hexahydrofuro-, hexahydropyrano-, and tetrahydrobenzofuroquinolines from N,N-dimethylaniline N-oxides and various electron-rich olefins in a tandem Polonovski-Povarov sequence is reported. Following activation of the N-O bond with Boc2O, an exocyclic iminium ion is unveiled upon exposure to tin(IV) chloride. A formal inverse-electron-demand aza-Diels-Alder cyclization generates the tetrahydroquinoline core of 29 examples in up to 92% yield.
- Bush, Timothy S.,Yap, Glenn P. A.,Chain, William J.
-
supporting information
p. 5406 - 5409
(2018/09/13)
-
- Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides
-
The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
- Reed, Hayley,Paul, Tyler R.,Chain, William J.
-
p. 11359 - 11368
(2018/08/06)
-
- Aromatic nitriles synthetic method of the compound (by machine translation)
-
The invention relates to an aromatic nitrile compound synthetic methods, is to benzaldehyde or a benzene ring substituted benzaldehyde derivatives as raw materials, in the catalysis of hydrazine hydrate, with ammonia reaction under normal temperature, adding sodium thiosulfate for removing excess iodine, adding pure water, for extractant, product and then with anhydrous sodium sulfate as the drying agent, using a rotary evaporation instrument rotary drying solvent, to obtain the product. The method of mild reaction conditions, without using a metal catalyst, operation is simple and easy, and the adaptability of the wide range of the substrate and the like, can be used for preparing different substituents on the benzene ring of the aromatic nitrile compounds. (by machine translation)
- -
-
Paragraph 0021
(2018/03/13)
-
- Direct synthesis of nitriles from aldehydes and hydroxylamine hydrochloride catalyzed by a HAP@AEPH2-SO3H Nanocatalyst
-
We describe an efficient method for the direct preparation of nitriles from aldehydes and hydroxylamine hydrochloride catalyzed by sulfonated nanohydroxyapatite functionalized by 2-aminoethyl dihydrogen phosphate (HAP@AEPH2-SO3H) as an eco-friendly and recyclable solid acid nanocatalyst. In this protocol the use of a solid acid nanocatalyst provides a green, useful, and rapid method for the preparation of nitriles in excellent yields. In addition, the notable feature of this methodolgy is that the synthesized nanocatalyst can be recovered and reused five times without any noticeable loss of efficiency.
- Masjed, Samane Memar,Akhlaghinia, Batool,Zarghani, Monireh,Razavi, Nasrin
-
-
- One-pot conversion of aldehydes to nitriles mediated by TiCl4
-
A simple and convenient one-pot synthesis of nitriles from the corresponding aliphatic and aromatic aldehydes has been developed. The titanium tetrachloride assisted reaction was conducted in pyridine under mild conditions using various types of aldehyde precursors and gave the corresponding nitriles in excellent yields. The application of the adopted protocol to isolated aldoxime intermediates provided the corresponding nitriles with yields comparable to those using the one-pot procedure.
- Leggio, Antonella,Belsito, Emilia Lucia,Gallo, Sonia,Liguori, Angelo
-
supporting information
p. 1512 - 1514
(2017/03/23)
-
