cas 6125-63-9, (E)-3-(2-furyl)acrylonitrile

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Preparation method of nitrile compound
The present invention belongs to the field of organic synthesis technology, specifically relates to a method for preparing a nitrile compound, aldehyde oxime derivatives as raw materials, adding DPPA and DBU, reacting in an organic solvent, one step to pr
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Paragraph 0072-0074

(2022/01/08)

Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy
Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.
Takahashi, Yoshiyuki,Tsuji, Hiroaki,Kawatsura, Motoi
p. 2654 - 2665
(2020/02/04)

Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
supporting information
p. 6046 - 6050
(2018/09/27)

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
supporting information
p. 2793 - 2796
(2018/06/25)

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
p. 107 - 118
(2017/09/28)

Preparation method of trans-alpha, beta-unsaturated nitriles compound
The invention relates to a preparation method of a trans-alpha, beta-unsaturated nitriles compound. The method comprises the following steps: uniformly mixing a benzyl alcohol compound, acetonitrile, a promoter and alkali, and carrying out reflux reaction completely to obtain reaction liquid; carrying out conventional extraction, drying, concentration and column chromatographic separation on the reaction liquid in sequence to obtain the trans-alpha, beta-unsaturated nitriles compound. The preparation method belongs to double-component one-boiler reaction, so that conditions are relatively mild, and raw materials are easy to prepare and readily available; the operation is simple, the yield is relatively high, and greenness, environment friendliness and economy can be realized; large-scale production can be realized; the preparation method has an extremely good application potential on the aspect of fine chemicals, and has a relatively good industrial application prospect.
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Paragraph 0066-0068

(2017/05/18)

Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)-Catalyzed Synthesis of Primary Pyridinylamines
A relay formalism is proposed herein for categorizing the interplay among reactants, target product, and catalytic center in transition-metal catalysis, an important factor that can dictate overall catalysis viability and efficiency. In this formalism, transition-metal catalysis can proceed by dissociative relay, associative covalent relay, and associative dative relay modes. An intriguing associative covalent relay process operates in rhodium(III)-catalyzed oxadiazolone-directed alkenyl C?H coupling with alkynes and allows efficient access to primary pyridinylamines. Although the primary pyridinylamine synthesis mechanism is posteriori rationalized, the relay formalism formulated herein can provide an important mechanistic conceptual framework for future catalyst design and reaction development.
Yu, Xiaolong,Chen, Kehao,Wang, Qi,Guo, Shan,Zha, Shanke,Zhu, Jin
supporting information
p. 5222 - 5226
(2017/04/27)

Rhodium(III)-catalyzed oxadiazole-directed alkenyl C-H activation for synthetic access to 2-acylamino and 2-amino pyridines
We report herein a Rh(III)-catalyzed alkenyl C-H activation protocol for the coupling of oxadiazoles with alkynes and synthesis of 2- acylamino and 2-amino pyridines, an important heterocyclic scaffold for various naturals products and synthetic pharmaceuticals bearing a readily reacting functional group. The selective protection/deprotection of amino groups through simple solvent switching, good functional group compatibility, superior product yield, and high regioselectivity are some of the notable synthetic features witnessed in this reaction protocol.
Yang, Fan,Yu, Jiaojiao,Liu, Yun,Zhu, Jin
supporting information
p. 9978 - 9987
(2018/05/31)

A Catalytic Peterson-like Synthesis of Alkenyl Nitriles
A heterogeneous fluoride catalyst was found to enable the straightforward formation of alkenyl nitriles from the reaction of aldehydes and simple or substituted acetonitriles, in the presence of commercially available silazanes and in solvent-free conditions. The protocol afforded the products in good to excellent yields with selectivity values dependent on the nature of the substrates. It represents an alternative to classic approaches using stoichiometric strong bases, and the catalyst can be easily recovered and reused for consecutive cycles.
Lanari, Daniela,Alonzi, Matteo,Ferlin, Francesco,Santoro, Stefano,Vaccaro, Luigi
supporting information
p. 2680 - 2683
(2016/06/15)

Cu-catalyzed debrominative cyanation of gem-dibromoolefins: A facile access to α,β-unsaturated nitriles
An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, l-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.
Ahuja, Brij Bhushan,Sudalai, Arumugam
p. 5918 - 5923
(2015/06/02)

Dual [Fe+Phosphine] catalysis: Application in catalytic wittig olefination
Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity was used within the context of catalytic Wittig olefination. Picture perfect: Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity is used within the context of catalytic Wittig olefination. EWG=Electron-withdrawing group.
Rommel, Susanne,Belger, Christian,Begouin, Jeanne-Marie,Plietker, Bernd
p. 1292 - 1301
(2015/04/27)

A facile, one-pot synthesis of β-substituted (Z)-acrylonitriles utilizing an α-diaminoboryl carbanion
A simple three-step single-pot procedure for Z-stereoselective synthesis of β-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated α-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products (up to 96:4 ratio) in good yields (80-98%).
Tomioka, Takashi,Takahashi, Yusuke,Vaughan, Trey G.,Yanase, Takayoshi
supporting information; experimental part
p. 2171 - 2173
(2010/07/08)

C-H activation reactions of ruthenium N-heterocyclic carbene complexes: Application in a catalytic tandem reaction involving C-C bond formation from alcohols
A series of ruthenium hydride N-alkyl heterocyclic carbene complexes has been investigated as catalysts for a tandem oxidation/Wittig/reduction reaction to give C-C bonds from alcohols. The C-H-activated carbene complex Ru(I iPr2Me2)′(PPh3) 2(CO)H (9) proves to be the most active precursor catalyzing the reaction of PhCH2OH and Ph3P=CHCN in 3 h at 70 °C. These results provide (a) a rare case in which N-alkyl carbenes afford higher catalytic activity than their N-aryl counterparts and (b) a novel example of the importance of NHC C-H activation in a catalytic cycle.
Burling, Suzanne,Paine, Belinda M.,Nama, Devendrababu,Brown, Victoria S.,Mahon, Mary F.,Prior, Timothy J.,Pregosin, Paul S.,Whittlesey, Michael K.,Williams, Jonathan M. J.
p. 1987 - 1995
(2007/10/03)

One-pot Wittig reactions in aqueous media: A rapid and environmentally benign synthesis of α,β-unsaturated carboxylic esters and nitriles
One-pot Wittig reactions of ethyl bromoacetate and bromoacetonitrile with aldehydes in the presence of PPh3 and LiOH in water were investigated. Most of the olefination reactions completed within 5-120 min in refluxing water containing 1.2 M LiCl to afford the olefin products in 71-97% yields with 100:0-55:45 ratios of E:Z isomers. Copyright Taylor & Francis Group, LLC.
Wu, Jinlong,Yue, Congyong
p. 2939 - 2947
(2007/10/03)

The one-pot Wittig reaction: A facile synthesis of α,β- unsaturated esters and nitriles by using nanocrystalline magnesium oxide
Nanocrystalline magnesium oxide was found to be an effective heterogeneous, solid base catalyst for the one-pot Wittig reaction to afford α,β-unsaturated esters and nitriles in excellent yields with high E-stereoselectivity in the presence of triphenylphosphine under mild conditions.
Choudary, Boyapati M.,Mahendar, Koosam,Kantam, M. Lakshmi,Ranganath, Kalluri V. S.,Athar, Taimur
p. 1977 - 1985
(2007/10/03)

Wittig reactions of stabilized phosphorus ylides with aldehydes in water
The Wittig reactions of three stabilized phosphorus ylides with aldehydes in water were investigated. Most of the olefination reactions completed within 5-60 min in refluxing water in the presence of 1.2 M LiCl to afford the olefin products in 65-98% yields. It was found that the Wittig reactions of stabilized phosphorus ylides with aldehydes in water were faster than those carried out in organic solvents. Copyright Taylor & Francis, Inc.
Wu, Jinlong,Zhang, Da,Wei, Shaoyong
p. 1213 - 1222
(2007/10/03)

Highly (Z)-selective synthesis of β-monosubstituted α,β-unsaturated cyanides using the peterson reaction
(Chemical Equation Presented) The Peterson reaction between (t-BuO)Ph 2SiCH2CN and various aldehydes furnishes the corresponding β-monosubstituted α,β-unsaturated cyanides with high Z selectivity (Z:E = 92:8 to >98:2).
Kojima, Satoshi,Fukuzaki, Tomohide,Yamakawa, Atsushi,Murai, Yutaka
p. 3917 - 3920
(2007/10/03)

Method for the synthesis of 2-(2-furyl)acrylonitriles
A new method was developed for the production of 2-(2-furl)acrylonitriles on the basis of the Schmidt reaction.
Pavlov
p. 1199 - 1202
(2007/10/03)

Solvents as Phase-transfer Catalysts in Reactions initiated by Solid Bases
For reactions initiated by solid bases (e.g. potassium hydroxide, sodium hydroxide, potassium carbonate), solvents (e.g. water, ButOH, polyethylene glycol, MeCN, Me2SO) may act as solid-liquid phase transfer catalysts (e.g. for C-H, N-H or O-H alkylation by alkyl halides, or epoxidation by sulfonium or sulfoxonium salts).
Bentley, T. William,Jones, Ray V. H.,Larder, Annette H.,Lock, Stephen J.
p. 2309 - 2310
(2007/10/02)

A Convenient Synthesis of α,β-Unsaturated Nitriles
α,β-Unsaturated nitriles were synthesized by the reaction of aldehydes with bromoacetonitrile promoted by tri-n-butylphosphine and zinc.
Zheng, Jianhua,Yu, Yang,Shen, Yanchang
p. 3277 - 3282
(2007/10/02)

Palladium-Catalyzed Furylation and Thienylation of Activated Alkenes with 2-Furoyl Chloride and 2-Thenoyl Chloride
2-Furoyl or 2-thenoyl chlorides readily react with activated alkenes in the presence of a tertiary amine and a catalytic amount of palladium(II) acetate to give 2-furylated or 2-thienylated alkenes.Under similar conditions, 2-benzofuroyl chloride undergoes facile alkenylation to produce 2-alkenylated benzofurans.The reaction involves a highly efficient decarbonylation of furoyl or thenoyl-palladium species.
Kasahara, Akira,Izumi, Taeko,Ogihara, Takao
p. 597 - 599
(2007/10/02)

SYNTHESIS OF α,β-UNSATURATED NITRILES BY REACTION OF HALOACETONITRILE WITH CARBONYL COMPOUNDS MEDIATED BY TRI-n-BUTYLSTIBINE
α,β-Unsaturated nitriles were synthesized by the reaction of haloacetonitriles with carbonyl compounds mediated by tri-n-butylstibine in excellent yields.
Huang, Yao-Zeng,Shen, Yanchang,Chen, Chen
p. 83 - 90
(2007/10/02)

SYNTHESIS AND THREE-DIMENSIONAL STRUCTURES OF 2-(2-FURYL)ACRYLONITRILES
Conditions for carrying out the Schmidt reaction that make it possible to obtain β-(2-furyl)acrylonitriles in high yields were found.It was shown by NMR and IR spectroscopy that the furylacrylonitriles obtained have an E-s-cis configuration.
Kul'nevich, V. G.,Pavlov, P. A.,Krapivin, G. D.
p. 943 - 945
(2007/10/02)

REACTIONS OF TRIETHYL PHOSPHITE WITH OXIMES OF α,β-UNSATURATED ALDEHYDES AND α-DICARBONYL COMPOUNDS
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Osipova, M. P.,Volkova, R. V.,Spiridonov, E. A.
p. 285 - 286
(2007/10/02)

Barium Hydroxide as Catalyst in Organic Reactions; V. Application in the Horner Reaction under Solid-Liquid Phase-Transfer Conditions
A new application of a barium hydroxide catalyst for the Horner reaction is described.The scope of the synthetic method is shown; furthermore, the yields are higher and the reaction times shorter than those previously reported for similar experimental conditions (solid-liquid).Ethyl 3-(1'-pyrenyl)-acrylate and the 3-(1'-pyrenyl)-acrylonitrile are described for the first time.
Sinisterra, J. V.,Mouloungui, Z.,Delmas, M.,Gaset, A.
p. 1097 - 1100
(2007/10/02)

Utilisation of 13C N.M.R. Spectroscopy for the Identification of E- and Z-α,β-Unsaturated Esters, Ketones and Nitriles.
Measurement of 3JCO,H coupling constants provides an unambiguous procedure for the configurational analysis of substituted 2- and 3-arylpropenoic esters and of E- and Z-2-arylbut-2-en-1,4-dioates, even when only one of the isomers is available for analysis.An analogous procedure can also be used for the configurational analysis of 3-arylpropenonitriles and of 4-arylbut-3-en-2-ones.
Gregory, Barrie,Hinz, Werner,Jones, R. Alan,Arques, Jose Sepulveda
p. 2801 - 2821
(2007/10/02)