- One-pot conversion of aromatic bromides and aromatics into aromatic nitriles
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Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with butyllithium and subsequently DMF, followed by treatment with molecular iodine in aqueous ammonia. The
- Ushijima, Sousuke,Togo, Hideo
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- Relative reactivity of anti- and syn-oximino carbonates and carbamates of 2-pyridylacetic acid esters
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(Matrix presented) anti-Oximes of 2-pyridylacetic acid esters are rapidly transformed to pyridine-2-carbonitrile under a variety of conditions while syn-oximes bearing tert-butyl esters can be conveniently deprotected to the corresponding carboxylic acid with subsequent fragmentation to the nitrile.
- Kim, Ha Young,Lantrip, Douglas A.,Fuchs, Philip L.
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- An improved Balz-Schiemann reaction enabled by ionic liquids and continuous processing
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A Balz-Schiemann reaction was developed to convert 2-cyano-5-aminopyridine to 2-cyano-5-fluoropyridine. The use of an ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate, BMIMBF4) as a solvent was found to be critical in achieving high assay yields and high selectivity for the fluorination vs. protonation. A process was developed to recycle and reuse the ionic liquid enabling its cost-effective use as a solvent. Finally, the optimal conditions were demonstrated under as a continuous process to address process safety risks associated with diazonium intermediates and the product was used to access a key intermediate in the synthesis of β-amyloid cleaving enzyme 1 inhibitor, verubecestat.
- Snead, David R.,Lévesque, Fran?ois,Morris, William J.,Naber, John R.
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- General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
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A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
- Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
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- Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides
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An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110°C) compared with the Rose-nmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions.
- Cristau, Henri-Jean,Ouali, Armelle,Spindler, Jean-Francis,Taillefer, Marc
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- Silica supported potassium oxide catalyst for dehydration of 2-picolinamide to form 2-cyanopyridine
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The dehydration of 2-picolinamide to produce 2-cyanopyridine was investigated thoroughly using silica supported potassium oxide as a heterogeneous catalyst. Both large specific surface area and pore size of SiO2 (B) contributed to the favorable catalytic performance for the synthesis of 2-CP. In addition, the yield of 2-CP showed the linear relationship with the amounts of medium basicity of the catalysts, demonstrating that medium basic sites were the active sites of silica supported potassium oxide catalysts. The catalysts were further characterized by XRD and FT-IR to clarify the active species. The results indicated the Si–O–K group produced by the reaction of K2CO3 with Si–OH was the active species, which was further evidenced by the adjustment of the amount of Si–OH by silylation and hydroxylation procedure.
- Li, Yamei,Zhao, Yujun,Wang, Shengping,Ma, Xinbin
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- Synthesis, characterization and crystal structure of 2-pyridinecarboxamide
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2-Pyridinecarboxamide was synthesized from 2-picoline through two-steps reaction. Initially, 2-picoline was converted into 2-cyanopyridine by ammoxidation in a stainless-steel fixed-bed reactor at 370 oC with V2O5 loaded on TiO2 as catalyst. The 2-cyanopyridine was transformed into 2-pyridinecarboxamide through oxidation hydrolysis in basic solution using MnO2 as oxidant at 70 oC. The final product was characterized by FT-IR, NMR and UV-visible analysis, and 2-pyridinecarboxamide in the final product was determined using HPLC. The crystal structure of 2-pyridinecarboxamide was investigated using X-ray diffraction and SHELX 2018/3 (sh) software and the result indicated that 2-pyridinecarboxamide crystallized in the monoclinic system, space group P21/n with a = 5.207(2), b = 7.097(3), c = 16.243(6) ?, V = 595.7 (4) ?3; Z = 4.
- Sun, Kai-Jin,Cai, Zhao-Sheng
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- A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides
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Deoxygenation of heteroaromatic N-oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N-oxide derivatives under mild conditions. A diverse range of mono- and bis N-oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N-oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring.
- Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.
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- Biomimetic models of nitric oxide synthase for the oxidation of oximes to carbonyl compounds catalyzed by water-soluble manganese porphyrins in aqueous solution
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A mild green and efficient approach for hydrogen peroxide oxidative converting oximes to the corresponding carbonyl compounds with a water-soluble manganese porphyrin as catalyst in water/acetone mixture has been developed. The water-soluble manganese porphyrin showed an excellent activity for the oxidative deoximation reactions of various oximes under ambient conditions in the absence of any additive. The oxidative deoximation was through the formation of high valent oxo-manganese species, which was confirmed by in situ UV-vis spectroscopy.
- Ren, Qing-Gang,Zhou, Xian-Tai,Ji, Hong-Bing
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- Tandem oxidation processes: The direct conversion of activated alcohols into nitriles
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The direct conversion of primary alcohols into nitriles is reported (RCH2OH into RCN) using manganese dioxide and ammonia in 2-propanol - THF, containing magnesium sulfate at room temperature. This transformation, which proceeds via an in situ
- McAllister, Graeme D.,Wilfred, Cecilia D.,Taylor, Richard J. K.
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- Ceria-catalyzed conversion of carbon dioxide into dimethyl carbonate with 2-cyanopyridine
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DMC run: Carbon dioxide can be converted into dimethyl carbonate in a reaction system involving 2-cyanopyridine as a dehydration agent, catalyzed by CeO2. Regeneration of the coproduct 2-picolinamide can be achieved over a Na2O/SiO2 catalyst. As a whole, the system servest to react carbon dioxide with methanol to produce dimethyl carbonate. Copyright
- Honda, Masayoshi,Tamura, Masazumi,Nakagawa, Yoshinao,Sonehara, Satoru,Suzuki, Kimihito,Fujimoto, Ken-Ichiro,Tomishige, Keiichi
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- Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis
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A protocol for the hydrodehalogenation of halogenated pyridines and quinolines by the sodium borohydride/N,N,N′,N′-tetramethylethylenediamine (NaBH4-TMEDA) system under palladium catalysts is reported. Catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II) in combination with NaBH4-TMEDA rapidly hydrodehalogenate chloro(bromo)-pyridines and -quinolines at room temperature in quantitative yields. Chemoselective reduction of 4,7-dichloroquinoline affords 7-chloroquinoline as the sole product in almost quantitative yield. Moreover, palladium(II) acetate-triphenylphosphine and NaBH4-TMEDA are able to reduce efficiently reactive bromo-pyridines and -quinolines.
- Chelucci, Giorgio
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- Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters
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The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.
- Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong
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- 2-tert-Butyl-5-(2-pyridyl)-2H-tetrazole as a chelating ligand in the direct synthesis of novel Cu(ii) and heterobimetallic Cu(ii)/Mn(ii) complexes
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For the first time, a representative of the 2,5-disubstituted tetrazoles, namely, 2-tert-butyl-5-(2-pyridyl)-2H-tetrazole (L), has been found to participate in oxidative dissolution of copper powder in homometalic systems Cu0-L-NH4X-DMSO (X = Cl, SCN, ClO4) and heterobimetallic ones Cu0-Mn(OAc)2-L-NH 4OAc-Solv (Solv = DMSO, DMF), providing the formation of molecular homometallic complexes [CuL2Cl2] (1), [CuL 2(SCN)2] (2), and [CuL2(H2O)] (ClO4)2 (3), heterobimetallic complex [Cu 2MnL2(OAc)6] (4) from DMF solution and its mixture with complex [Cu2MnL2(OAc)6] ·2DMSO (5) from DMSO solution. Free ligand L and complexes 1-4 were characterized by elemental analysis, IR spectroscopy, thermal and X-ray single crystal analyses, whereas complex 5 was characterized by X-ray analysis only. Compounds 1-3 are mononuclear complexes, with chelating coordination mode of L via the tetrazole ring N4 and pyridine ring N7 atoms. Heterobimetallic complexes 4 and 5 possess trinuclear structures, with a linear Cu-Mn-Cu arrangement of the metal atoms, linked by the acetate anions; each copper(ii) atom is decorated by a chelating unit of L via the tetrazole ring N1 and pyridine ring N7 atoms in complex 4, and via the N4, N7 atoms in complex 5. Temperature-dependent magnetic susceptibility measurements of complex 4 revealed a weak antiferromagnetic coupling between the paramagnetic copper(ii) and manganese(ii) ions (J = -2.5 cm-1, gCu = 2.25 and gMn = 2.01), with magnetic exchange through the acetato bridges.
- Mosalkova, Anastasiya P.,Voitekhovich, Sergei V.,Lyakhov, Alexander S.,Ivashkevich, Ludmila S.,Lach, Jochen,Kersting, Berthold,Gaponik, Pavel N.,Ivashkevich, Oleg A.
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- Importance of Acidity on an Energetically Unfavorable Electron-Transfer Reaction-An Extension of the Rehm-Weller Equation. Photoreaction of Triplet 2,4-Pyridinedicarbonitrile with 2-Propanol
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An electron spin resonance study of the radical formed when 2,4-pyridinedicarbonitrile (1) is irradiated in the cavity of an ESR spectrometer has been done and the values of the ?-spin populations on the ring atoms were determined from the measured proton and nitrogen couplings.Radicals were generated by in situ photolysis of deaerated solutions of 1.The rate of radical formation was measured in acetonitrile at 33 deg C with varying amounts of 2-propanol, water, and hydrochloric acid.Quenching and photosensitization studies show the triplet state of 1 to be the photoreactive state. ΔGet values calculated by the Rehm-Weller equation were found to be endoergic when either the T1 or the T2 state of 1 is involved.Evidence is presented which supports a mechanism in which N-H bond formation is coupled to the electron-transfer step, resulting in an exoergic process.N-H bond formation becomes the driving force for the reaction.
- Caronna, Tullio,Morrocchi, Sergio,Vittimberga, Bruno M.
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- One-pot conversion of aromatic bromides and aromatics into aromatic nitriles via aryllithiums and their DMF adduct
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Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3. The same treatment of typical aromatics and heteroaromatics with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3 also provided the corresponding aromatic nitriles in good yields. Moreover, the same treatment of aromatic bromides and aromatics with half amount of DIH (1,3-diiodo-5,5- dimethylhydantoin) instead of molecular iodine worked effectively to give the corresponding aromatic nitriles, respectively, in good yields. These reactions are novel and environmentally benign one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, respectively, through the formation of aryllithiums and their DMF adducts.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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- Nitrile Synthesis via Desulfonylative-Smiles Rearrangement
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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
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p. 4460 - 4467
(2022/03/15)
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- A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide
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This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.
- ULUDAG, Nesimi,GIDEN, Ozge NUR
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p. 993 - 998
(2021/02/05)
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- Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
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A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
- Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
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- Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide
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Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]
- Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng
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- Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile
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A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.
- Liu, Si-Zhan,Li, Jing,Xue, Cao-Gen,Xu, Xue-Tao,Lei, Lin-Sheng,Huo, Chen-Yu,Wang, Zhen,Wang, Shao-Hua
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supporting information
(2021/02/01)
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- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
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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
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p. 17288 - 17292
(2020/05/18)
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- Technology for continuously synthesizing 2-cyanopyridine
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The invention discloses a technology for continuously synthesizing 2-cyanopyridine. The technology comprises following steps: (1) ammonia oxidation of 2-pyridine carboxamide: raising the temperature of a reactor with a catalyst to 350-400 DEG C, introducing oxygen-containing gas, ammonia gas, and 2-pyridine carboxamide into the reactor to carry out reactions, wherein the mole ratio of oxygen-containing gas: ammonia gas: 2-pyridine carboxamide is 100: 10-20: 1-2, and introducing generated reactive gas to next section; and (2) condensing the reactive gas generated in the step (1), layering the condensate in a layering kettle, making 2-cyanopyridine in the lower layer stay in the layering kettle for 2 to 30 minutes, continuously pumping 2-cyanopyridine in the lower layer into a rectifying still, and carrying out rectification to obtain a finished product of 2-cyanopyridine. By optimizing the gas ratio and other reaction conditions, the final conversion rate of 2-pyridine carboxamide is greater than 98%, and the 2-cyanopyridine yield is larger than 86%.
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Paragraph 0037-0047
(2020/02/27)
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- An Air-Stable N-Heterocyclic [PSiP] Pincer Iron Hydride and an Analogous Nitrogen Iron Hydride: Synthesis and Catalytic Dehydration of Primary Amides to Nitriles
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An air-stable N-heterocyclic PSiP pincer iron hydride FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) (4) was synthesized by Si-H activation of a Ph-substituted [PSiP] pincer ligand. The analogous strong electron-donating iPr-substituted [PSiP] pincer ligand was prepared and introduced into iron complex to give an iron nitrogen complex FeH(N2)(PMe3)(SiPh(NCH2PiPr2)2C6H4) (6). Both 4 and 6 showed similar high efficiency for catalytic dehydration of primary amides to nitriles. Air-stable iron hydride 4 was the best catalyst for its stabilization and convenient preparation. A diverse range of cyano compounds including aromatic and aliphatic species was obtained in moderate to excellent yields. A plausible catalytic reaction mechanism was proposed.
- Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Wang, Yajie,Xie, Shangqing,Zhang, Hua
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- Lewis acid promoted dehydration of amides to nitriles catalyzed by [PSiP]-pincer iron hydrides
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The dehydration of primary amides to their corresponding nitriles using four [PSiP]-pincer hydrido iron complexes 1–4 [(2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (2), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3)2 (3) and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (4)] as catalysts in the presence of (EtO)3SiH as dehydrating reagent was explored in the good to excellent yields. It was proved for the first time that Lewis acid could significantly promote this catalytic system under milder reaction conditions than other Lewis acid-promoted system, such as shorter reaction time or lower reaction temperature. This is also the first example that dehydration of primary amides to nitriles was catalyzed by silyl hydrido iron complexes bearing [PSiP]-pincer ligands with Lewis acid as additive. This catalytic system has good tolerance for many substituents. Among the four iron hydrides 1 is the best catalyst. The effects of substituents of the [PSiP]-pincer ligands on the catalytic activity of the iron hydrides were discussed. A catalytic reaction mechanism was proposed. Complex 4 is a new iron complex and was fully characterized. The molecular structure of 4 was determined by single crystal X-ray diffraction.
- Chang, Guoliang,Li, Xiaoyan,Zhang, Peng,Yang, Wenjing,Li, Kai,Wang, Yajie,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
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- An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions
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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.
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p. 1640 - 1645
(2020/10/22)
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- A Versatile VMPO Catalyst Prepared In Situ for Oxidative Ammonolysis of Isomeric Picolines and Xylenes
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Abstract: The V2O5–MoO3–P2O5 (VMPO) catalyst has been prepared in situ by thermal decomposition of vanado-molybdophosphoric acid (PMoV) on TiO2 support at 475°C. The TiO2 supported VMPO catalysts are characterized by FT–IR, XRD, BET surface area, NH3–TPD, and H2–TPR. Morphology of the catalyst has been studied by TEM. The accumulated data indicate decomposition of PMoV and presence of phosphate and pyrophosphate phases of molybdenum and vanadium after calcination. TPD and TPR studies exhibit the moderate acidity and presence of V4+ in the material, respectively. The VMPO catalyst has been used for ammoxidation of six different compounds including three isomeric picolines and three isomeric xylenes to the corresponding nitriles with the yield of 90–96%.
- Dutta, P.,Pathak, D. D.,Senapati, Rabinarayan
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p. 292 - 298
(2020/04/17)
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- Aerobic oxidation of primary benzylic amines to amides and nitriles catalyzed by ruthenium carbonyl clusters carrying N,O-bidentate ligands
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Four trinuclear ruthenium carbonyl clusters, (6-BrPyCHRO)2Ru3(CO)8 (R = 4-OCH3C6H4, 1a; R = 4-BrC6H4, 1b) and (2-OC6H4-HCN-C6H4R)2Ru3(CO)8 (R = 4-OCH3, 2a; R = 4-Br, 2b), were synthesized from the reactions of Ru3(CO)12 with the corresponding N,O-bidentate ligands (two pyridyl alcohols and two Schiff bases) respectively in a ratio of 1:2. Three new complexes 1b, 2a and 2b have been fully characterized by elemental analysis, FT-IR, NMR and X-ray crystallography. The catalytic activity of these ruthenium complexes for the aerobic oxidation of primary benzylic amines to amides and nitriles in the presence of t-BuOK was investigated, of which the Schiff base complex 2a was found to exhibit the highest activity.
- Dong, Qing,Han, Zhangang,Hao, Zhiqiang,Li, Ying,Lin, Jin,Lu, Guo-Liang,Meng, Lizhen,Yan, Xinlong
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p. 3480 - 3487
(2020/04/02)
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- Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
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Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
- Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
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p. 13481 - 13494
(2020/12/15)
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- Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction
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The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.
- Shah, Sk. Sheriff,Shee, Maniklal,Singh, N. D. Pradeep
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supporting information
p. 4240 - 4243
(2020/04/22)
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- Method for preparing aryl primary amide by adopting metal-catalyzed one-pot method
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The invention discloses a method for synthesizing aryl primary amide by adopting a metal-catalyzed one-pot method. The method comprises the steps of: taking aryl bromidess as raw materials, allowing the aryl bromidess to react with a cyanide source under the action of a palladium catalyst, substituting bromine on an aromatic ring with cyano to obtain cyano aromatic hydrocarbon, directly adding anaqueous solution of alkali into the reaction solution without aftertreatment, and carrying out hydrolysis reaction to obtain aryl primary amide. Compared with the prior art, the method for preparing aryl primary amide from the aryl bromides has the advantages of the short synthesis route, fewer reaction steps, simple operation, mild conditions, the high conversion rate, low toxicity and industrialproduction potential.
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Paragraph 0026; 0027
(2020/04/06)
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- Efficient dehydration of primary amides to nitriles catalyzed by phosphorus-chalcogen chelated iron hydrides
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A series of phosphorus-chalcogen chelated hydrido iron (II) complexes 1–7, (o-(R'2P)-p-R-C6H4Y)FeH (PMe3)3 (1: R = H, R' = Ph, Y = O; 2: R = Me, R' = Ph, Y = O; 3: R = H, R' = iPr, Y = O; 4: R = Me, R' = iPr, Y = O; 5: R = H, R' = Ph, Y = S; 6: R = Me, R' = Ph, Y = S; 7: R = H, R' = Ph, Y = Se), were synthesized. The catalytic performances of 1–7 for dehydration of amides to nitriles were explored by comparing three factors: (1) different chalcogen coordination atoms Y; (2) R' group of the phosphine moiety; (3) R substituent group at the phenyl ring. It is confirmed that 5 with S as coordination atom has the best catalytic activity and 7 with Se as coordination atom has the poorest catalytic activity among complexes 1, 5 and 7. Electron-rich complex 4 is the best catalyst among the seven complexes and the dehydration reaction was completed by using 2 mol% catalyst loading at 60 °C with 24 hr in the presence of (EtO)3SiH in THF. Catalyst 4 has good tolerance to many functional groups. Among the seven iron complexes, new complexes 3 and 4 were obtained via the O-H bond activation of the preligands o-iPr2P(C6H4)OH and o-iPr2P-p-Me-(C6H4)OH by Fe(PMe3)4. Both 3 and 4 were characterized by spectroscopic methods and X-ray diffraction analysis. The catalytic mechanism was experimentally studied and also proposed.
- Li, Kai,Sun, Hongjian,Yang, Wenjing,Wang, Yajie,Xie, Shangqing,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
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- Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides
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A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.
- Murata, Yuki,Iwasa, Hitomi,Matsumura, Mio,Yasuike, Shuji
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p. 679 - 681
(2020/07/30)
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- Metal-free dehydrosulfurization of thioamides to nitriles under visible light
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A visible light-mediated, metal-free dehydrosulfurization reaction of thioamides to nitriles is described. This reaction features high yields, mild reaction conditions, and the use of a cheap organic dye as the photoredox catalyst and air as the oxidant.
- Xu, Tianxiao,Cao, Tianpeng,Feng, Qingyuan,Huang, Shenlin,Liao, Saihu
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supporting information
p. 5151 - 5153
(2020/05/26)
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- Continuous-flow synthesis of nitriles from aldehydes via Schmidt reaction
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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
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p. 973 - 976
(2019/01/29)
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- Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles
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Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one-pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.
- Gurjar, Jitendra,Bater, Jorick,Fokin, Valery V.
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supporting information
p. 1906 - 1909
(2019/01/24)
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- Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
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A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
- Fang, Wan-Yin,Qin, Hua-Li
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p. 5803 - 5812
(2019/05/14)
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- SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles
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A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.
- Ding, Chengrong,Mei, Guangyao,Wang, Haibo,Zhang, Guofu,Zhao, Yiyong
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p. 1484 - 1488
(2019/07/15)
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- Method for preparing nitrile
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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.
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Paragraph 0015
(2019/06/13)
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- Dehydration of primary amides to nitriles catalyzed by [CNC]-pincer hydrido cobalt(III) complexes
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The dehydration reactions from primary amides to nitriles were catalyzed by the [CNC]-pincer hydrido cobalt(III) complexes [(ortho-F4C6–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (1), [(2,5-F2C6H2–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (2) and [(2,4,5-F3C6H–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (3) as catalysts with (EtO)3SiH as an efficient reducing agent. These hydrido cobalt(III) complexes as catalysts are suitable for many substrates and have good functional group tolerance. Among the three cobalt hydrides, complex 2 is the best catalyst. This is the first hydrido cobalt complex-catalyzed dehydration of primary amides to nitriles.
- Ren, Shishuai,Wang, Yangyang,Yang, Fei,Sun, Hongjian,Li, Xiaoyan
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- METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONATE ESTER
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Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.
- -
-
Paragraph 0098-0109
(2019/07/03)
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- METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONIC ACID ESTER
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Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.
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Paragraph 0152-0154
(2020/01/08)
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- A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide
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This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96percent) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.
- Uludag, Nesimi,Nur Giden, Ozge
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p. 993 - 998
(2020/06/27)
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- Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
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A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
- Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 520 - 525
(2018/12/13)
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- Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
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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
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- Iron and Phenol Co-Catalysis for Rapid Synthesis of Nitriles under Mild Conditions
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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
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p. 4617 - 4623
(2019/07/15)
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- Synthesis of silyl iron hydride: Via Si-H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides
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The hydrido silyl iron complex (o-Ph2PC6H4SiMe2)Fe(PMe3)3H (2) was obtained via the activation of the Si-H bond of the bidentate silyl ligand o-Ph2P(C6H4)SiMe2H (1) by Fe(PMe3)4. 2 showed good to excellent catalytic activity in both the reduction of aldehydes/ketones and the dehydration of benzamide. In addition, with complex 2 as a catalyst, α,β-unsaturated carbonyls could be selectively reduced to the corresponding α,β-unsaturated alcohols. The mechanisms of the formation of 2 and the catalytic dehydration process are proposed and partly experimentally verified.
- Ren, Shishuai,Xie, Shangqing,Zheng, Tingting,Wang, Yangyang,Xu, Shilu,Xue, Benjing,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter
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p. 4352 - 4359
(2018/03/26)
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- Production technology of 2,2'-bipyridine
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The invention discloses a production technology of 2,2'-bipyridine, and belongs to the field of chemical synthesis. The production technology comprises the following steps: with acetonitrile and acetylene as starting raw materials, performing cyclization under the catalysis of bis(cyclopentadienyl) cobalt to produce 2-methylpyridine, then performing a reaction on the 2-methylpyridine and ammonia gas under the catalysis of tetraphenylporphyrin cobalt to produce 2-cyanopyridine, and finally performing cyclization on the 2-cyanopyridine and acetylene under the catalysis of bis(cyclopentadienyl) cobalt to produce the 2,2'-methylpyridine. The production technology is safe and low in cost, few solid, liquid and gas wastes are produced, and the production technology is suitable for industrial production.
- -
-
Paragraph 0028; 0035; 0038
(2018/11/03)
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- Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality
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A ruthenium(II) complex bearing a naphthyridine-functionalized pyrazole ligand catalyzes oxidant-free and acceptorless selective double dehydrogenation of primary amines to nitriles at moderate temperature. The role of the proton-responsive entity on the ligand scaffold is demonstrated by control experiments, including the use of a N-methylated pyrazole analogue. DFT calculations reveal intricate hydride and proton transfers to achieve the overall elimination of 2 equiv of H2.
- Dutta, Indranil,Yadav, Sudhir,Sarbajna, Abir,De, Subhabrata,H?lscher, Markus,Leitner, Walter,Bera, Jitendra K.
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supporting information
p. 8662 - 8666
(2018/07/09)
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- Nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine
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A nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine (TCT) using aminoacetonitrile as the cyanating agent is described. This catalytic system delivered the desired products in moderate to good yields with good substrate compatibility. The readily available starting materials, cost-effective nickel catalyst and metal-free cyanating agent are the major features of the present method.
- Wang, Liang,Wang, Yaoyao,Shen, Jun,Chen, Qun,He, Ming-Yang
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supporting information
p. 4816 - 4820
(2018/07/13)
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- Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
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The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
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Paragraph 0043; 0045; 0175-0177
(2018/11/03)
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- Direct synthesis of nitriles from aldehydes and hydroxylamine hydrochloride catalyzed by a HAP@AEPH2-SO3H Nanocatalyst
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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
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- A scalable production of anisonitrile through organoselenium-catalyzed dehydration of anisaldoxime under solventless conditions
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An organoselenium-catalyzed dehydration reaction of anisaldoxime to produce the useful fine chemical anisonitrile was achieved under solventless conditions without using any dehydrant. Simple PhSe(O)OH could be employed as the recyclable and reusable catalyst without obvious deactivation, and the reaction generated no wastes at all. By an easily operable distillation process, the product could be isolated in high purity, as confirmed by NMR spectroscopic analysis. The reaction was scalable to at least kilogram-scale with excellent carbon mass balance at 99.3%, showing very great potential of the method in industrial-scale production. The mechanism of the reaction was also discussed based on the experimental findings.
- Jing, Xiaobi,Wang, Tingting,Ding, Yuanhua,Yu, Lei
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p. 107 - 111
(2017/05/19)
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- Facile and efficient preparation of nitriles through FeCl4–IL–SiO2-catalyzed direct oxidation of alcohols with hydrogen peroxide
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Abstract: A series of silica-supported functionalized ionic liquids catalysts have been prepared and tested in the oxidative conversion of alcohols to nitriles with H2O2 as the oxidant. The features of this heterogeneous reaction system were studied by tuning various reaction parameters including catalyst selection, amount of the catalyst, and effect of solvents. Among the catalysts, FeCl4–IL–SiO2 exhibited the highest efficiency in direct oxidation of alcohols to nitriles under the optimized condition along with good recycle performance. Also, a possible catalytic mechanism is provided. Graphical abstract: [Figure not available: see fulltext.]
- Hu, Yu-Lin,Wang, Bing Tong,Fang, Dong
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p. 233 - 243
(2017/01/05)
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- A primary alcohol nitrile method (by machine translation)
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The invention discloses a catalytic oxidation of primary alcohol nitrile method, said method comprising the following steps: formula (I) or formula (III) as shown in the primary alcohol as the raw material, in order to copper salt as catalyst, in order to air as the oxidizing agent, in order to TEMPO (2, 2, 6, 6 - tetramethyl piperidine nitrogen oxide) and help the oxidizing agent, ammonia as cocatalyst and solvent, for 80 - 120 °C reaction under 15 - 30h, after the reaction, the resulting reaction solution by the following formula (II) after treatment of the formula (IV) is shown in the nitriles; the reaction of the invention conversion, high yield, easy operation, low cost, safe reaction, the whole process is friendly to the environment, pollution-free. (by machine translation)
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Paragraph 0080; 0081; 0082; 0083; 0084
(2017/07/22)
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- Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli–Cushman Reaction of Unprotected Oximes
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The first application of multicomponent chemistry (the Castagnoli–Cushman reaction) toward the convenient one-step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron-binding com
- Bakulina, Olga,Bannykh, Anton,Dar'in, Dmitry,Krasavin, Mikhail
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p. 17667 - 17673
(2017/12/26)
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- A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines
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Herein is reported the design and application of a reagent for the direct functionalization of pyridines. These reactions occur under mild conditions and exhibit broad functional group tolerance, enabling the late-stage functionalization of drug-like molecules. The reagent can be easily prepared on large scale from inexpensive reagents, and reacts in the title reaction with acetonitrile, sodium chloride, and sodium methanesulfonate as the sole byproducts. Although this Communication focuses primarily on reactions with cyanide as nucleophile, preliminary experiments with other nucleophiles foreshadow the broad reaching synthetic utility of this approach.
- Fier, Patrick S.
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p. 9499 - 9502
(2017/07/24)
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- Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature
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The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).
- Kim, Kicheol,Hong, Soon Hyeok
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supporting information
p. 2345 - 2351
(2017/07/22)
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- Synthesis of nitriles from aldehydes with trimethylphenylammonium tribromide and ammonium acetate
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Various aromatic and heterocyclic aldehydes were easily converted to respective nitriles with the combination of trimethylphenylammonium tribromide and ammonium acetate in good yields at room temperature.
- Sayama, Shinsei
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p. 1796 - 1802
(2016/11/06)
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