- Design, Synthesis, and Pharmacological Activity of a New Matrix Metalloproteinase-9 Inhibitor
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The new MMP-9 inhibitor 1-{4-[(4-chlorobenzoyl)amino]phenyl}sulfonyl-L-proline, with a theoretical inhibition constant of IC50 = 4 × 105 M, was constructed on the basis of structural requirements for selective inhibitors of gelatinases. This constructed compound and its close structural analogs were synthesized and these substances were found to have low toxicity, (LD50 > 300 mg/kg). The new inhibitor given p.o. at a dose of 20 mg/kg/day on the background of acute myocardial infarction significantly decreased the content of immunoreactive MMP-9 in plasma in rats, to the level obtained with doxycycline.
- Grigorkevich,Mokrov,Dyabina,Stolyaruk,Tsorin,Ionova,Kryzhanovskii,Gudasheva,Durnev
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Read Online
- Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
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A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.
- Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
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supporting information
p. 4843 - 4848
(2021/06/28)
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- Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids
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A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.
- Tang, Jing-Jing,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
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p. 13955 - 13961
(2021/11/20)
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- Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
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A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
- Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
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supporting information
p. 15117 - 15127
(2021/10/25)
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- Iron-catalyzed oxidative amidation of acylhydrazines with amines
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A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
- Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
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- Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
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N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
- Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong
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supporting information
p. 6227 - 6232
(2021/07/28)
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- Fe-mediated synthesis of: N -aryl amides from nitroarenes and acyl chlorides
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Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of N-aryl amides. Starting from commercially available nitroarenes and acyl halides, N-aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.
- Wu, Yundong,Guo, Lei,Liu, Yuxuan,Xiang, Jiannan,Jiang, Jun
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p. 15290 - 15295
(2021/05/19)
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- Chromium-catalyzed ligand-free amidation of esters with anilines
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Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.
- Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 762 - 766
(2021/04/14)
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- Selective hydrogenation dehalogenation method of ortho-halogenated acylaniline
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The invention discloses a selective hydrogenation dehalogenation method of copper-catalyzed ortho-halogenated acylaniline. The method comprises the following steps: by using ortho-halogenated acylaniline as a starting raw material and copper acetylacetonate/vasicine as a catalyst, adding an organic alkali, reacting in an alcoholic solution at 80-100 DEG C for 12 hours, and regioselectively catalytically hydrogenating ortho-bromine and iodine atoms. The preparation method has the characteristics of simplicity and convenience in operation, wide substrate application range, low cost, high regioselectivity and the like, and has practicability.
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Paragraph 0069-0073
(2021/01/20)
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- Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source
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In present work, we have explored a Cu(acac)2/vasicine-catalyzed regioselective hydrodehalogenation methodology of o-haloanilides using EtOH as hydrogen source and solvent. The catalytic system could selectively dehalogenate 2-Br and 2-I, and features regioselective, efficient and functional group tolerance.
- Li, Min-Xin,Li, Mei-Ling,Tang, Yan-Ling,Sun, Yun,Qu, Lu,Huang, Feng,Mao, Ze-Wei
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supporting information
(2021/05/03)
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- Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications
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Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.
- Angeles-Beltrán, Deyanira,Mendoza-Espinosa, Daniel,Rendón-Nava, David,Rheingold, Arnold L.
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supporting information
p. 2166 - 2177
(2021/07/20)
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- Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
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A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
- Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
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supporting information
(2020/12/21)
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- Green synthetic method of N-arylamides using recyclable cheap metal catalyst
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Magnetically separable and reusable Fe/Cu oxide (Fe3O4-Cu2O) nanoparticles were employed as an efficient catalyst for the arylation of benzamide, which was carried out with a range of both arylboronic acid and benzamide to afford N-arylamide in good to excellent yield.
- Wang, Xingyang,Liu, Jianhui,An, Guanghui
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supporting information
(2020/10/05)
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- α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
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Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
- Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
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p. 7433 - 7445
(2020/06/27)
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- Decarboxylative/Oxidative Amidation of Aryl α-Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium
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The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
- Barak, Dinesh S.,Dahatonde, Dipak J.,Dighe, Shashikant U.,Kant, Ruchir,Batra, Sanjay
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supporting information
p. 9381 - 9385
(2020/11/30)
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- Nickel/briphos-catalyzed transamidation of unactivated tertiary amides
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The transamidation of tertiary amides was achieved via nickel catalysis in combination with briphos ligands. N-Methyl-N-phenylbenzamide derivatives reacted with primary amines in the presence of NiCl2/briphos L4 to provide the transamidated products in moderate to good yields. Primary aromatic amines delivered higher product yields than aliphatic amines.
- Kim, Hyunwoo,Lee, Sunwoo,Shin, Taeil,Yang, Dahyeon
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supporting information
p. 6053 - 6057
(2020/10/27)
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- Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides
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A Cu-catalyzed oxidative amidation of simple ketones with amines via carbon-carbon (C-C) bond cleavage has been developed. A number of aryl and alkyl ketones could be easily converted to amides using cheap copper salt as the catalyst and O2 as the oxidant with a wide range of amines, including primary and secondary amines. This method shows a notable advantage of the broad scope for the substrate, thus providing a practical approach to amides. A plausible mechanism is proposed based on the preliminary experiments.
- Li, Ke,Liu, Wei,Liu, Yu-Feng,Yang, Guo-Ping,Zeng, Kai
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p. 6958 - 6964
(2020/10/02)
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- Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)
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Although highly effective for most amide syntheses, the activation of carboxylic acids requires the use of problematic coupling reagents and is often poorly suited for challenging cases such as N-methyl amino acids. As an alternative to both secondary and tertiary amides, we report their convenient synthesis by the rapid oxidation of trifluoroborate iminiums (TIMs). TIMs are easily prepared by acid-promoted condensation of potassium acyltrifluoroborates (KATs) and amines and are cleanly and rapidly oxidized to amides with hydrogen peroxide. The overall transformation can be conducted either as a one-pot procedure or via isolation of the TIM. The unique nature of the neutral, zwitterionic TIMs makes possible the preparation of tertiary amides via an iminium species that would not be accessible from other carbonyl derivatives and can be conducted in the presence of unprotected functional groups including acids, alcohols and thioethers. In preliminary studies, this approach was applied to the late-stage modifications of long peptides and the iterative synthesis of short, N-methylated peptides without the need for coupling agents.
- Bode, Jeffrey W.,Ryan, Sarah J.,Schuhmacher, Anne,Shiro, Tomoya
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p. 7609 - 7614
(2020/08/14)
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- Efficient Pd-Catalyzed Hydrodehalogenation of o -Haloanilides in Water
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In the present work, we have developed a practical methodology for the hydrodehalogenation of o -haloanilides using PdCl 2at 100 °C under mild conditions in water. The catalytic system could selectively dehalogenate both aryl chloride and aryl bromide and exhibit a broad functional group tolerance.
- Gao, Hui,Li, Minxin,Mao, Zewei,Rao, Gaoxiong,Tang, Yanling
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supporting information
p. 1121 - 1125
(2020/07/03)
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- Visible Light-Induced Amide Bond Formation
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A metal-, base-, and additive-free amide bond formation reaction was developed under an organic photoredox catalyst. This green approach showed excellent functional selectivity without affecting other functional groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. This method featured a broad substrate scope, good compatibility with water and air, and high yields (≤95%). The potential utilities were demonstrated by the synthesis of important drug molecules such as paracetamol, melatonin, moclobemide, and acetazolamide.
- Song, Wangze,Dong, Kun,Li, Ming
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supporting information
p. 371 - 375
(2019/11/29)
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- Method for preparing amide by visible light-induced metal-free participation (by machine translation)
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The method for preparing the amide in the, preparation method of the novel amide disclosed by the invention has the advantages that, the reaction: conditions are mild, the 9 - reaction conditions are mild, and the yield 71%. of the reaction conditions is not lower than the reaction conditions . (by machine translation)
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Paragraph 0107-0110
(2020/02/14)
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- N-heterocyclic carbene palladium complex crystal, synthetic method thereof, and application thereof in preparation of amide compounds
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The invention discloses an N-heterocyclic carbene palladium complex crystal, a synthetic method thereof and application thereof in preparation of amide compounds. The structural formula of the complexcrystal is shown in the specification, or the complex crystal is prepared from an N-heterocyclic carbene ligand, Pd(CH3CN)2Cl2 and Ag2O in acetonitrile serving as a solvent. The N-heterocyclic carbene palladium complex crystal is relatively stable, wherein the raw materials used in the synthesis method are cheap and easy to obtain, so that the synthetic method is simple, convenient and easy to implement is simple in post-treamtent and is high in yield; and the N-heterocyclic carbene palladium complex crystal is used for catalyzing carbonylation carbon-nitrogen bond coupling reaction to prepare amide compounds and is high in catalytic activity, easy to operate and high in atom economy.
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Paragraph 0029-0032; 0043-0046
(2019/12/02)
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- Method for synthesizing amide compound through photocatalysis in water phase
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The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
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Paragraph 0018-0049
(2019/10/01)
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- Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene
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Cyrene as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.
- Bousfield, Thomas W.,Pearce, Katharine P. R.,Nyamini, Simbarashe B.,Angelis-Dimakis, Athanasios,Camp, Jason E.
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supporting information
p. 3675 - 3681
(2019/07/09)
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- Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
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Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
- Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 237 - 241
(2019/01/10)
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- Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes
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Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.
- Ling, Liang,Chen, Changpeng,Luo, Meiming,Zeng, Xiaoming
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supporting information
(2019/03/19)
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- Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride
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A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.
- Zhang, Jin,Hou, Yanyan,Ma, Yangmin,Szostak, Michal
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p. 338 - 345
(2019/01/10)
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- Secondary/tertiary amide compound and synthesis method thereof
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The invention discloses a secondary/tertiary amide compound and a synthesis method thereof. The method comprises the following steps: adding arylsilane and an amine compound, a catalyst and an additive to a solvent, introducing CO under a certain pressure, carrying out a carbonylation reaction, and carrying out separation and purification to obtain the secondary/tertiary amide. The method for preparing the secondary/tertiary amide by the carbonylation reaction has the advantages of concision, high efficiency, directness in the reaction, high atom economy, and wide sources and good stability ofa substrate. The reaction system of the invention does not require inert gas protection, and has mild conditions, and the target product is easy to separate and the yield reaches up to 92% under optimized reaction conditions.
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Paragraph 0131; 0132; 0133; 0134
(2019/01/21)
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- Vilsmeier-Haack reagent mediated synthetic transformations with an immobilized iridium complex photoredox catalyst
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An immobilized iridium complex photocatalyst Ir(ppy)2(PDVB-py) was synthesized by immobilization of the iridium complex onto the nanoporous vinylpyridine-divinylbenzene copolymer (PDVB-py). Its application for the synthesis of amides, nitriles, and anhydrides was reported via reactions under the action of the visible-light-driven in situ generated Vilsmeier-Haack reagent from CBr4 in DMF. The results showed that this heterogeneous photocatalyst has extremely high activity and excellent stability to be recycled five times.
- Zhi, Peng,Xi, Zi-Wei,Wang, Dan-Yan,Wang, Wei,Liang, Xue-Zheng,Tao, Fei-Fei,Shen, Run-Pu,Shen, Yong-Miao
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p. 709 - 717
(2019/01/10)
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- Synthesis and Catalytic Applications of Palladium(II) Complexes Supported by Hydroxyl-Functionalized Triazolylidenes
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A series of allyl (1–3) and cinnamyl (4–6) palladium(II) complexes supported by hydroxyl functionalized triazolylidenes have been prepared. All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, FT-IR and elemental analyses. The new triazolylidene palladium complexes were tested as precatalysts in the coupling of aryl chlorides with boronic acids and the coupling of esters with amines to produce biphenyls and amides, respectively. According to the overall results, complexes 4 and 5 displayed the highest catalytic activity in both coupling processes, providing good to excellent yields under mild reaction conditions and using a wide range of substrates.
- De la Fuente-Olvera, Agustín A.,Suárez-Castillo, Oscar R.,Mendoza-Espinosa, Daniel
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supporting information
p. 4879 - 4886
(2019/12/11)
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- Carbon bridged bis-amide-based rare-earth amine compound and its preparation and with [...][...] synthesis reaction in the application of the
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The invention discloses a carbon-bridged diacylamino rare earth amide with a general formula of {LLn[N(SiMe3)2]}2, wherein Ln is a rare earth metal selected from lanthanum, neodymium, samarium and yttrium, L represents a carbon-bridged diacylamino ligand, and n may be 1, 2 or 3 and can represent different ligands. The chemical structural formula of the carbon-bridged diacylamino rare earth amide differs with changes of the rare earth metal and the ligand. The invention targetedly discloses four chemical structural formulas of the rare earth amide as shown in the general formula. The carbon-bridged diacylamino rare earth amide provided by the invention is simple to synthesize, has definite structure and high yield and is easy to separate and purify. The invention also provides a preparation method for the rare earth amide and a method for applying the rare earth amide as a catalyst for catalysis of amidation of aldehyde and amine. The application method has the advantages of mild conditions, high activity, good selectivity, a wide substrate adaptation scope, a small catalyst amount and high product yield.
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Paragraph 0112; 0113
(2019/04/02)
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- The magnetic graphene oxide/NHC catalyzed aerobic direct amidation and cross-dehydrogenative coupling of aldehydes
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In this paper, the synthesis of a novel imidazolium based N-heterocyclic carbene (NHC) containing imidazopyridine substitutes using a three-component reaction is described. This compound was immobilized on magnetic graphene oxide (GO) to make a heterogeneous catalyst for the direct aerobic amidation of benzaldehyde derivatives under solvent-free conditions, as well as the intra-and intermolecular cross dehydrogenative coupling of aldehydes. In addition, the catalytic activity of the NHC catalyst was homogeneously studied in the presence of Fe3O4 nanoparticles under the same conditions, and showed good activity with lower yields than the heterogeneous catalyst.
- Sepahvand, Heshmatollah,Ghasemi, Elnaz,Sharbati, Mohammad,Mohammadi, Melika Sadat,Arshadi Pirlar, Maghsoud,Shahverdizadeh, Gholam Hossein
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p. 16555 - 16565
(2019/11/11)
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- Pd-Catalyzed Oxidation of Aldimines to Amides
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Methods for the synthesis of amides via the direct oxidation of imines are rarely reported. Here we report an efficient method for Pd-catalyzed oxidation of imines to amide derivatives by the use of cheap aqueous tert -butyl hydroperoxide as an oxidant through a Wacker-type reaction. This method is practically convenient and displays high functional group tolerance, allowing a variety of imines to transform into the corresponding amide derivatives in moderate to good yields.
- Gao, Shanshan,Ma, Yaorui,Chen, Weidong,Luo, Junfei
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supporting information
p. 2191 - 2194
(2018/10/02)
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- Synthesis of Secondary Amides through the Palladium(II)-Catalyzed Aminocarbonylation of Arylboronic Acids with Amines or Hydrazines and Carbon Dioxide
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A new Pd-catalyzed aminocarbonylation of arylboronic acids with amines or phenylhydrazines has been developed. Various secondary amides were produced from readily available substrates and cheap common metal catalysts in a CO atmosphere (balloon). Remarkably, we presents the first example of aminocarbonylations between arylboronic acids and phenylhydrazines.
- Zhang, Jin,Ma, Yuqiang,Ma, Yangmin
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supporting information
p. 1720 - 1725
(2018/04/24)
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- N-aryl secondary aryl amide synthetic method
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The invention discloses an N-aryl secondary aryl amide synthetic method. The synthetic method is characterized in that arylboronic acid and aromatic primary amine, and a main catalyst and a cocatalystare added in a solvent, then the components are subjected to a carbonylation reaction and then separation and purification to obtain the N-aryl secondary aryl amide, and CO is introduced into a reaction system during a reaction process so that the pressure of the reaction system is 0.1-5 MPa. The synthetic method is concise and efficient, aromatic amine and organic boric acid and CO which are stable in air and easily available can be taken as the reaction raw materials, under existence of the solvent, the catalysts are added, and the secondary aryl amide is synthesized with high efficiency under mild reaction condition.
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Paragraph 0077; 0078; 0079; 0080; 0081
(2018/03/28)
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- Integration of co2 reduction with subsequent carbonylation: Towards extending chemical utilization of co2
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Currently, it still remains a challenge to amplify the spectrum of chemical fixation of CO2, although enormous progress has been achieved in this field. In view of the widespread applications of CO in a myriad of industrial carbonylation processes, an alternative strategy is proposed in which CO2 reduction to CO is combined with carbonylation with CO generated ex situ, which affords efficiently pharmaceutically and agrochemically attractive molecules. As such, CO2 in this study was efficiently reduced by triphenysilane using CsF to CO in a sealed two-chamber reactor. Subsequently, palladium-catalyzed aminocar-bonylation, carbonylative Sonogashira coupling of aryl iodides, and rhodium(I)-mediated Pauson–Khand-type reaction proceeded smoothly to yield amides, alkynones, and bicyclic cy-clopentenones, respectively. Furthermore, the formed alkynones can further be successfully converted to a series of heterocycles, for example, pyrazoles, 3a-hydroxyisoxazolo[3,2-a]isoindol-8-(3aH)-one derivatives and pyrimidines in moderate yields. The striking features of this protocol include operational simplicity, high efficiency, and relatively broad application scope, which represents an alternative avenue for CO2 transformation.
- Lang, Xian-Dong,He, Liang-Nian
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- Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides
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A practical and efficient method for N-arylation of benz-amides promoted by potassium carbonate in the presence of DMEDA was developed. The reaction was carried out without addition of any transition-metal catalyst to afford a variety of N-arylated products in moderate to good yields (up to 97%).
- Huang, Fei,Wu, San,Hu, Weiye,Zhang, Songlin
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supporting information
p. 1090 - 1096
(2017/11/29)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 6404 - 6407
(2017/12/08)
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- Photocatalytic benzene and benzene derivative direct hydroxylation or amination method
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The invention discloses a photocatalytic benzene and benzene derivative direct hydroxylation or amination method. The method is characterized by comprising the following steps: (1) adding a photo-sensitizer and a cobalt catalyst into a solvent to obtain a solution (A); (2) adding benzene (or benzene derivatives), water, ammonia gas, and amide derivatives (or sulfonamide derivatives) into the solution (A) to obtain a solution (B); and (3) in a N2 (or Ar) environment, radiating the solution (B) by a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, or an LED lamp to obtain phenols or amines and H2. For the first time, a photo-sensitizer and a cobalt catalyst are combined and applied to photocatalytic hydroxylation and amination of benzene. The conditions of the method are mild, light is taken as the driving energy, no oxidant is added, the only byproduct is H2, and the whole process is green, concise, and efficient. High selective benzene one-step hydroxylation to generate phenol or high selective phenol/benzene one-step amination to generate aniline is realized, and the method can be applied to the production of phenol and aniline.
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Paragraph 0150-0151
(2017/11/29)
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- A Cross-Coupling Approach to Amide Bond Formation from Esters
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A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation in the absence of harsh bases.
- Ben Halima, Taoufik,Vandavasi, Jaya Kishore,Shkoor, Mohanad,Newman, Stephen G.
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p. 2176 - 2180
(2017/08/09)
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- Synthesis of N -Aryl Amides by Ligand-Free Copper-Catalyzed ipso -Amidation of Arylboronic Acids with Nitriles
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A facile copper-catalyzed ipso-amidation of arylboronic acids with nitriles has been developed. The method provides a highly efficient and economical synthesis of N-aryl amides with a broad substrate scope.
- Qiao, Yan,Li, Gaoqiang,Liu, Sha,Yangkai, Yujie,Tu, Jingxuan,Xu, Feng
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supporting information
p. 1834 - 1838
(2017/04/06)
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- Efficient Friedel–Crafts benzoylation of aniline derivatives with 4-fluorobenzoyl chloride using copper triflate in the synthesis of aminobenzophenones
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ABSTRACT: An efficient pathway for the synthesis of the aminobenzophenone derivatives via Friedel–Crafts benzoylation using copper triflate as catalyst is proposed. New derivatives are synthesized. The copper triflate could be easily recovered and reused without loss of catalytic activity. Both the use of ionic liquids and microwave heating turned out to be fruitful.
- Tran, Phuong Hoang,Phung, Huy Quang,Hansen, Poul Erik,Tran, Hai Ngoc,Le, Thach Ngoc
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p. 893 - 901
(2016/07/06)
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- Acidylation method of amine
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The invention discloses an acidylation method of amine.The method includes the following steps that amine derivatives, hydrazide derivatives, organic peroxide and a catalyst are dissolved in a solvent and react at the temperature of 40-80 DEG C, and amide derivatives are obtained.The amide derivatives and hydrazide derivatives serve as initiators, the raw materials are easy to obtain and the number of varieties is large.Products obtained through the method are diverse in type, can be directly used and can also be used for other further reactions.The method is mild in reaction condition, simple in reaction operation and post-processing process, high in product yield and suitable for scale production.
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Paragraph 0042
(2016/10/10)
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- Peroxide-mediated direct synthesis of amides from aroyl surrogates
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An efficient and metal-free method has been developed for the direct synthesis of amides from readily available azobenzenes reacting with aroyl surrogates such as alcohols, methylarenes. A variety of amides were afforded in moderate to good yields through this reaction. It is another example reported by our group for the use of azobenzene as the new radical acceptor.
- Hong, Gang,Wu, Shengying,Zhu, Xiaoyan,Mao, Dan,Wang, Limin
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p. 436 - 441
(2015/12/31)
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- Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C–H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones
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An efficient ligand-free copper-manganese (Cu-Mn) spinel oxide-catalyzed direct tandem C?H oxygenation and N-arylation of benzylamines has been developed. The method has been utilized for the synthesis of medicinally important 2-arylquinazolin-4(3H)-ones. Salient features of this method include recyclable catalyst, no ligand, excellent product yields, shorter reaction times and a broad substrate scope. (Figure presented.).
- Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
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supporting information
p. 3027 - 3033
(2016/10/09)
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- Detection of weak hydrogen bonding to fluoro and nitro groups in solution using H/D exchange
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Hydrogen/deuterium (H/D) exchange can be a sensitive technique for measuring the strength of hydrogen bonding to neutral organic nitro and fluoro groups. The slower rates of reaction in comparison to suitable controls suggest that hydrogen bonding is present, albeit rather weak.
- Shugrue,Defrancisco,Metrano,Brink,Nomoto,Linton
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supporting information
p. 2223 - 2227
(2016/03/01)
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- Effective nitration of anilides and acrylamides by tert-butyl nitrite
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Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.
- Ji, Yi-Fei,Yan, Hong,Jiang, Qi-Bai
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p. 2051 - 2060
(2015/03/18)
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- An efficient magnetic copper ferrite nanoparticle catalysed ligand and solvent free synthesis of N-aryl amide from aldoximes and iodobenzene
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A simple, efficient, and environmentally benign method has been reported for the synthesis of N-aryl amides using aldoximes and iodobenzene under ligand free and solvent free conditions and using magnetically separable copper ferrite nanoparticles as catalyst. The catalyst was characterised using XRD, FEG-SEM, EDAX, ICP-AES and TEM and tested for recyclability for up to five cycles.
- Sarode, Sachin A.,Bhojane, Jeevan M.,Nagarkar, Jayashree M.
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p. 105353 - 105358
(2015/12/30)
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- Palladium/copper tandem catalysis for carbon-carbon triple bond cleavage of diaryl acetylenes
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A method for carbon-carbon triple bond cleavage based on palladium/copper tandem catalysis is developed. In this chemistry, anilines and diaryl acetylenes were converted into benzamides through cascade transformations combining palladium-catalyzed hydroamination of alkyne with copper-catalyzed aerobic oxidative C-C bond cleavage.
- Wang, Zhiwei,Fan, Wenyou,Deng, Guo-Jun,Zhou, Wang
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supporting information
p. 5449 - 5452
(2015/09/15)
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- Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
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A general copper/air catalytic system for selectively oxidative C-C bond cleavage of 1,2-diarylethan-1-one has been developed, giving aromatic aldehydes and N-benzoylation products of various amines in moderate to excellent yields. This research provides an alternative approach for the N-benzoylation of amine in mild and neutral conditions.
- Fan, Wenyou,Yang, Youqing,Lei, Jianhua,Jiang, Qijian,Zhou, Wang
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p. 8782 - 8789
(2015/09/15)
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