- Carbon monoxide free aminocarbonylation of aryl and alkenyl iodides using DMF as an amide source
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(figure presented) R = aryl or alkenyl Palladium-catalyzed coupling reaction of N,N-dimethylformamide with aryl or alkenyl halides successfully proceeded in the presence of phosphoryl chloride to afford the corresponding tertiary amides in good yields.
- Hosoi, Kazushi,Nozaki, Kyoko,Hiyama, Tamejiro
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- Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere
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Amidation of nitrile with N,N-dimethylformamide (DMF) was catalyzed by Cu2O with 1,10-phenanthroline as a ligand under an oxygen atmosphere. A variety of N,N-dimethyl benzamides were obtained in yields up to 84%.
- Hu, Chenxu,Yan, Xufei,Zhou, Xiangge,Li, Zhengkai
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- Amidation reaction of carboxylic acid with formamide derivative using SO3?pyridine
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The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3?py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.
- Kawano, Shota,Saito, Kodai,Yamada, Tohru
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- Silicadiphenyl phosphinite (SDPP)/Pd(0) nanocatalyst for efficient aminocarbonylation of aryl halides with POCl3 and DMF
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Silicadiphenyl phosphinite (SDPP) as a new phosphorylated silica and catalytic amounts of Pd(II) generates nano SDPP/Pd(0) catalyst for the efficient aminocarbonylation of aryl halides in the presence of POCl3 and N,N-dimethylformamide (DMF). Amides are obtained in high yields from aryl iodides and also activated aryl bromides, chlorides.
- Iranpoor, Nasser,Firouzabadi, Habib,Motevalli, Somayeh
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- Vinyl-λ3-iodanes act as efficient sulfur atom acceptors: Vinylic SN2-based strategy for conversion of tertiary thioamides to amides
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Exposure of tertiary thioamides to (E)-1-hexenyl(phenyl)-λ3-iodane results in vinylic SN2 reaction to give the inverted (Z)-S-vinylthioimidonium salts, which under alkaline hydrolysis (Na2CO3 or K2CO
- Ochiai, Masahito,Yamamoto, Shinji
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- Pd/C: an efficient, heterogeneous and reusable catalyst for carbon monoxide-free aminocarbonylation of aryl iodides
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Carbon monoxide-free aminocarbonylation is carried out efficiently via coupling of N,N-dimethylformamide (DMF) with aryl iodides using Pd/C as a heterogeneous catalyst. The catalyst exhibits remarkable activity and is reusable for up to three consecutive cycles. The reaction is applicable to a wide variety of substituted aryl iodides with different steric and electronic properties providing excellent yields of the corresponding tertiary amides.
- Tambade, Pawan J.,Patil, Yogesh P.,Bhanushali, Mayur J.,Bhanage, Bhalchandra M.
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- Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols and N-substituted Formamides Using a Co–Al Based Heterogeneous Catalyst
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Present work reports the direct synthesis of amides from oxidative coupling of benzyl alcohols with various N-substituted formamides using a cobalt-hydrotalcite (Co-HT) derived catalyst. The Co-HT derived catalysts (Co-HT-2, Co-HT-3 and Co-HT-4 having Co2+/Al3+ molar ratio in the catalyst preparation mixture as 1/1, 2/1 and 3/1 respectively) were prepare following a co-precipitation method and characterized well by powder XRD, XPS, FEG-SEM, EDS, DTG–TGA, FT-IR and N2 physisorption measurements. A range of functional amides were obtained in good yields from oxidative coupling of various substituted benzyl alcohols and a range of N-substituted formamides using Co-HT-3 catalyst and oxidant TBHP. Mechanistic investigation suggests that the amidation reaction is associated with the formation and coupling of radical species. Furthermore, the Co-HT derived catalyst was easily recoverable and recyclable with retained high catalytic activity towards the oxidative coupling of benzyl alcohol with DMF. Graphical Abstract: [Figure not available: see fulltext.].
- Subhedar, Dnyaneshwar D.,Gupta, Shyam Sunder R.,Bhanage, Bhalchandra M.
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- Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides
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We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.
- Boyle, Mhairi,Livingstone, Keith,Henry, Martyn C.,Elwood, Jessica M. L.,Lopez-Fernandez, J. Daniel,Jamieson, Craig
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supporting information
p. 334 - 338
(2022/01/20)
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- Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines
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Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.
- Yi, Jaeeun,Kim, Hyun Tae,Jaladi, Ashok Kumar,An, Duk Keun
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supporting information
p. 129 - 132
(2021/11/17)
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- One-pot synthesis of a highly disperse core-shell CuO-alginate nanocomposite and the investigation of its antibacterial and catalytic properties
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In this study, sodium alginate was extracted from Sargassum algae, collected from coastal waters of Bushehr, Persian Gulf, Iran and used as a stabilizing and wrapping agent for CuO nanoparticles. The synthesized nanocomposite was characterized by some spectroscopic and microscopic techniques, such as IR, XRD, Uv-vis, BET, BJH, zeta potential, SEM, TEM, HR-TEM, and XPS. The antibacterial effects of the CuO-alginate nanocomposite against some bacteria, isolated from a burn wound, were evaluated. The results showed that this nanocomposite had better antibacterial effects than its components onPseudomonas aeruginosaATCC 27853,Staphylococcus aureusATCC 12600,Streptococcus pyogenesATCC 19615, andStaphylococcus epidermidisATCC 49461. Among these,Staphylococcus aureusATCC 12600 was the most sensitive one to this nanocomposite, with the lowest minimum inhibitory concentration (2.08 mg mL?1) observed. Moreover, the synthesized nanocomposite showed good catalytic activity in the oxidative coupling of carboxylic acids withN,N-dialkylformamides toward the synthesis of amides.
- Habibi, Hassan,Mansourinejhad, Sanam,Saberi, Dariush,Shadi, Ahmad
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p. 199 - 211
(2021/12/30)
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- Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination
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Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.
- Tan, Xuefeng,Massignan, Leonardo,Hou, Xiaoyan,Frey, Johanna,Oliveira, Jo?o C. A.,Hussain, Masoom Nasiha,Ackermann, Lutz
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supporting information
p. 13264 - 13270
(2021/05/06)
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- Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
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We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
- Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
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- Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes
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Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.
- Chen, Xuenian,Kang, Jia-Xin,Ma, Yan-Na,Miao, Yu-Qi
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supporting information
p. 3595 - 3599
(2021/06/06)
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- Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
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An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
- Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
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supporting information
p. 4583 - 4587
(2020/05/05)
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- Direct and Selective C-H Carbamoylation of (Hetero)aromatics with TMSOTf-Activated Carbamoyl Chloride
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Exploiting trimethylsilyltrifluoromethanesulfonate as Lewis acid, (hetero)aromatics underwent regioselective and direct carbamoylation. The method is based on the in situ generation of a highly electrophilic carbamoyl triflate active species.
- Uehara, Ayaka,Olivero, Sandra,Michelet, Bastien,Martin-Mingot, Agnès,Thibaudeau, Sébastien,Du?ach, Elisabet
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supporting information
p. 46 - 49
(2018/11/27)
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- Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
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A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.
- Haydl, Alexander M.,Hartwig, John F.
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supporting information
p. 1337 - 1341
(2019/02/26)
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- HALOALLYLAMINE PYRAZOLE DERIVATIVE INHIBITORS OF LYSYL OXIDASES AND USES THEREOF
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The present invention relates to novel compounds which are capable of inhibiting certain amine oxidase enzymes. These compounds are useful for treatment of a variety of indications, e.g., fibrosis, cancer and/or angiogenesis in human subjects as well as i
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Paragraph 0219
(2018/09/20)
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- Nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source
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The nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source is developed. The procedure can prepare both tertiary and secondary amides, and is applicable to various carbamoylsilanes and aryl halides containing differen
- Wen, Xue-Ping,Han, Yu-Ling,Chen, Jian-Xin
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p. 45107 - 45112
(2017/10/13)
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- Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors
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Oxidative amidation is a valuable process for the transformation of oxygenated organic compounds to valuable amides. However, the reaction is severely limited by the use of an expensive catalyst and limited substrate scope. To circumvent these limitations, designing a transition-metal-based nanocatalyst via more straightforward and economical methodology with superior catalytic performances with broad substrate scope is desirable. To resolve the aforementioned issues, we report a facile method for the synthesis of nanocatalysts NiO and CuO by the sol-gel-assisted thermal decomposition of complexes [Ni(hep-H)(H2O)4]SO4 (SSMP-1) and [Cu(μ-hep)(BA)]2 (SSMP-2) [hep-H = 2-(2-hydroxylethyl)pyridine; BA = benzoic acid] as single-source molecular precursors (SSMPs) for the oxidative amidation of benzyl alcohol, benzaldehyde, and BA by using N,N-dimethylformamide (DMF) as the solvent and as an amine source, in the presence of tert-butylhydroperoxide (TBHP) as the oxidant, at T = 80 °C. In addition to nanocatalysts NiO and CuO, our previously reported Co/CoO nanocatalyst (CoNC), derived from the complex [CoII(hep-H)(H2O)4]SO4 (A) as an SSMP, was also explored for the aforementioned reaction. Also, we have carefully investigated the difference in the catalytic performance of Co-, Ni-, and Cu-based nanoparticles synthesized from the SSMP for the conversion of various oxygenated and unsaturated organic compounds to their respective amides. Among all, CuO showed an optimum catalytic performance for the oxidative amidation of various oxygenated and unsaturated organic compounds with a broad reaction scope. Finally, CuO can be recovered unaltered and reused for several (six times) recycles without any loss in catalytic activity.
- Mohammad, Akbar,Chandra, Prakash,Ghosh, Topi,Carraro, Mauro,Mobin, Shaikh M.
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p. 10596 - 10608
(2017/09/12)
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- Oxidative amidation of benzaldehydes and benzylamines with: N -substituted formamides over a Co/Al hydrotalcite-derived catalyst
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The present work describes a highly efficient synthetic strategy for amides via oxidative coupling of benzaldehydes or benzylamines with N-substituted formamides using a heterogeneous Co/Al hydrotalcite-derived catalyst in the presence of TBHP. A series of Co/Al hydrotalcite-derived catalysts (Cat-2, Cat-3, and Cat-4 with the Co2+/Al3+ molar ratio in the synthesis mixture as 1/1, 2/1 and 3/1) have been prepared by a simple co-precipitation method and characterized using powder XRD, XPS, FEG-SEM, EDS, FT-IR, DTG-TGA and N2 physical adsorption techniques. Among the as-prepared catalysts, Cat-3 exhibited excellent catalytic activity towards the direct amidation of benzaldehydes as well as benzylamines bearing various substituents into the corresponding amides at 100 °C using TBHP as an oxidant. The mechanistic investigation of the amidation reaction revealed that the reaction follows a radical pathway. Furthermore, the catalyst is easily separable and recyclable without considerable loss in catalytic activity.
- Gupta, Shyam Sunder R.,Nakhate, Akhil V.,Rasal, Kalidas B.,Deshmukh, Gunjan P.,Mannepalli, Lakshmi Kantam
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p. 15268 - 15276
(2017/12/15)
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- Palladium-Catalyzed Aminocarbonylation of Aryl Halides with 2,4,6-Trichloro-1,3,5-triazine/Formamide Mixed Reagent
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In this work, the mixture of formamide and 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride or TCT) is introduced as a new amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of a catalytic amount of palladium and TCT/formamide reagent, a range of aryl halides (X = Cl, Br, I) were converted into amides efficiently in N,N-dimethylformamide at 120 °C. The 2,4,6-trichloro-1,3,5-triazine/formamide mixed reagent was found to be an efficient amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of this reagent and a catalytic amount of Pd, a range of amides were synthesized by using aryl halides.
- Iranpoor, Nasser,Panahi, Farhad,Roozbin, Fatemeh,Erfan, Soodabeh,Rahimi, Sajjad
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p. 1781 - 1787
(2016/04/05)
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- Metal–Organic Framework Based on Copper and Carboxylate-Imidazole as Robust and Effective Catalyst in the Oxidative Amidation of Carboxylic Acids and Formamides
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A metal–organic framework (MOF) based on copper and 1,3-bis(carboxymethyl)imidazole (bcmim) was prepared on a gram scale by using a precipitation method at room temperature. The Cu(bcmim)2MOF was shown to be an efficient catalyst for the preparation of amides through an oxidative coupling between carboxylic acids and formamides in the presence of an oxidant, such as tert-butyl hydroperoxide (TBHP). The method for the preparation of the amides is robust regardless of the carboxylic acid and gives good conversions with good selectivity. The heterogeneous catalyst was recovered unaltered after the reaction, was easily separated from the reaction mixture, and subsequently reactivated by suitable treatment. Moreover, the coupling reaction was scaled up to a gram scale, which allowed for the preparation of valuable products, such as fatty acid amides (i.e., 1-palmitoylpiperidine).
- Albert-Soriano, María,Pastor, Isidro M.
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supporting information
p. 5180 - 5188
(2016/10/26)
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- General and efficient oxidative amidation of benzyl alcohols with amines using diacetoxyiodobenzene and TBHP
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A facile oxidative coupling of alcohols and amines to construct amides was developed using DIB as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. Various secondary and tertiary amides were prepared in good yield utilizing inexpensive and readily available reagents under mild reaction condition. The reaction involved operational simplicity, metal free oxidation, and wide functional group tolerance as attractive features.
- Sutar, Yogesh B.,Bhagat, Saket B.,Telvekar, Vikas N.
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p. 6768 - 6771
(2016/02/03)
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- Potassium tert-Butoxide-Mediated Amine Acyl Exchange Reaction of N,N-Disubstituted Formamides with Aromatic Carbonyl Derivatives via Sequential C-N Bond Cleavage/Formation: An Approach to Aromatic Amides
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A novel potassium tert-butoxide-mediated amine acyl exchange of N,N-disubstituted formamides with aromatic carbonyl derivatives in a sequential C-N bond cleavage/formation process leading to aromatic amides is described. This methodology tolerates a wide range of aromatic carbonyl compounds, including aromatic aldehydes, acyl chlorides, unactivated esters, and acid anhydrides. The usage of inexpensive and readily available reagents, broad substrate scope, and the simple, mild (50°C) and transition metal-free conditions make this protocol very practical. In addition, a plausible reaction mechanism is proposed on the basis of experimental observations.
- Zhang, Ming-Zhong,Guo, Qing-Hu,Sheng, Wen-Bing,Guo, Can-Cheng
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p. 2855 - 2861
(2015/09/28)
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- Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis
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Enabled by merging iridium photoredox catalysis and palladium catalysis, α-oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd0-PdII-PdIII pathway, in which the PdIII intermediate is responsible for reoxidizing IrII to complete the IrIII-IrIII-IrII photoredox cycle. Like a mergin': Enabled by merging iridium photoredox catalysis and palladium catalysis, palladium-catalyzed decarboxylative coupling of α-oxocarboxylates with aryl halides can proceed at room temperature. DFT calculations suggest that a Pd0-PdII-PdIII catalytic cycle is merged with an IrIII-IrIII-IrII photoredox cycle, in which PdIII is responsible for oxidizing IrII to complete the photoredox cycle.
- Cheng, Wan-Min,Shang, Rui,Yu, Hai-Zhu,Fu, Yao
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supporting information
p. 13191 - 13195
(2015/09/15)
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- Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts
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A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).
- Bai, Cuihua,Yao, Xianfang,Li, Yingwei
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p. 884 - 891
(2015/02/19)
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- N,N-Dimethylformamide solvothermal strategy: From fabrication of palladium nanoparticles supported on reduced graphene oxide nanosheets to their application in catalytic aminocarbonylation reactions
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A facile N,N-dimethylformamide (DMF) solvothermal strategy has been developed to fabricate palladium nanoparticles supported on reduced graphene oxide nanosheets (SRGO-Pd), which efficiently catalyze the aminocarbonylation of aryl halides. The palladium n
- Zhang, Ying,Sun, Huaming,Zhang, Weiqiang,Gao, Ziwei,Yang, Peng,Gu, Jian
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- Copper-catalyzed amide bond formation from formamides and carboxylic acids
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A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
- Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
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- A general continuous flow method for palladium catalysed carbonylation reactions using single and multiple tube-in-tube gas-liquid microreactors
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A series of continuous flow chemistry processes that facilitate the palladium-catalysed carbonylation of aryl and vinyl iodides and aryl bromides with a range of alkoxy, hydroxy and amino nucleophiles is reported. Harnessing a semipermeable Teflon AF-2400 Tube-in-Tube assembly, these reactors permit the controlled transport of carbon monoxide into solution at elevated pressure to generate homogeneous flow streams, avoiding some potential issues associated with segmented flow gas-liquid reactors. As the volume of pressurised gas contained within the device is low, the hazards associated with this are potentially mitigated relative to comparable batch processes. We also show how the incorporation of a second in-line gas-flow reactor allows for the sequential introduction of two gases (carbon monoxide and a gaseous nucleophile) into the reaction stream. A Teflon AF-2400 Tube-in-Tube reactor facilitates the use of carbon monoxide in continuous-flow C-C bond forming reactions providing esters, amides, carboxylic acids, lactones and lactams. Two reactors can be used in series to permit the sequential addition of two reactive gases (CO and Me2NH) into the flow stream.
- Gross, Ulrike,Koos, Peter,O'brien, Matthew,Polyzos, Anastasios,Ley, Steven V.
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supporting information
p. 6418 - 6430
(2016/02/18)
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- WCl6/DMF as a new reagent system for the phosphine-free Pd(0)-catalyzed aminocarbonylation of aryl halides
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WCl6 in dimethyl formamide (DMF) is introduced as a new reagent system for aminocarbonylation of aryl halides in the presence of PdCl2 as pre-catalyst without any phosphorous ligand. Aryl iodides, bromides as well as chlorides were efficiently converted to their corresponding N,N-dimethyl amides in good to high yields. In this protocol, WCl6/DMF is responsible for the generation of both Pd(0) catalyst as well as the formation of a Vilsmeier imminium type intermediate.
- Iranpoor, Nasser,Firouzabadi, Habib,Rizi, Zeinab Tavangar,Erfan, Soodabeh
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p. 43178 - 43182
(2015/02/19)
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- Syntheses of amides via iodine-catalyzed multiple sp3 C-H bonds oxidation of methylarenes and sequential coupling with N,N-dialkylformamides
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The oxidative coupling of methylarenes and N,N-dialkylformamides was developed, and the appropriate reaction conditions were established. By using I2 as the catalyst, and tert-butyl hydroperoxide (TBHP) as the oxidant, the reaction provided N,N
- Du, Bingnan,Sun, Peipei
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p. 1176 - 1182
(2014/08/18)
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- Oxidative synthesis of benzamides from toluenes and DMF
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An interesting oxidative procedure for the synthesis of benzamides has been developed through the cleavage of sp3CH bond of methyl arenes with N-substituted formamides. Various benzamides were prepared in low to moderate yields. Even though the
- Feng, Jian-Bo,Wei, Duo,Gong, Jin-Long,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 5082 - 5084
(2015/01/08)
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- Oxidative coupling of methylamine with an aminyl radical: Direct amidation catalyzed by I2/TBHP with HCl
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Oxidative coupling of methylamines with an aminyl radical to construct amides was developed in the presence of an I2/TBHP catalyst under acidic conditions via the two cleavages of the sp3 C-N bond of aryl-methylamines and the sp2 C-N bond of N-substituted formamides respectively. This transition-metal-free protocol provides a novel synthetic tool for the construction of N-substituted amides and a series of arylamides can be easily obtained with good yields. This journal is the Partner Organisations 2014.
- Gao, Lingfeng,Tang, Haoming,Wang, Zhiyong
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supporting information
p. 4085 - 4088
(2014/04/03)
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- A novel method for the conversion of carboxylic acids to N,N-dimethylamides using N,N-dimethylacetamide as a dimethylamine source
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A simple, cost effective and environmentally benign method is reported for the preparation of N,N-dimethylamides from carboxylic acids. The versatility of the method is determined by synthesising a large number of N,N-dimethylamide derivatives. Carboxylic acids are heated at 160-165°C in N,N-dimethylacetamide solvent in the presence of1,1'-carbonyldiimidazole to afford the corresponding N,N-dimethylamides in good to excellent yields.
- Aavula, Sanjeev Kumar,Chikkulapally, Anil,Hanumanthappa,Jyothi, Indira,Vinod,Sulur, Kumar,Manjunatha,Sythana, Suresh Kumar
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p. 155 - 159
(2013/07/11)
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- Electrochemical synthesis of amides: Direct transformation of methyl ketones with formamides
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A direct transformation from methyl ketones to secondary or tertiary amides has been developed through a novel electrochemical approach and a wide scope of formamides could be utilized as the amide sources. This transformation was promoted by in situ generated iodine through electrolysis of sodium iodide under mild, metal-free conditions. This electrochemical procedure could avoid the use of stoichiometric iodine and afforded the target products in good to excellent yields.
- Huang, Haolai,Yuan, Gaoqing,Li, Xianwei,Jiang, Huanfeng
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supporting information
p. 7156 - 7159
(2013/12/04)
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- Copper-catalyzed oxidative coupling of carboxylic acids with N,N-dialkylformamides: An approach to the synthesis of amides
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A new synthetic approach for amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. A new synthetic approach to amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst and aqueous tert-butyl hydroperoxide (TBHP) as a sacrificial oxidant. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. Copyright
- Kumar, P. Santhosh,Kumar, G. Sathish,Kumar, R. Arun,Reddy, N. Veera,Rajender Reddy
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supporting information
p. 1218 - 1222
(2013/04/10)
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- Copper-catalyzed amidation of acids using formamides as the amine source
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Copper-catalyzed amidation of acids with formamides or acetamide for the selective synthesis of amides with the aid of 1,4-diazabicyclo[2.2.2]octane as the ligand and tert-butyl hydroperoxide as the oxidant is presented. This method is highly compatible with a wide range of acids, including alkyl acids, aryl acids, α,β-unsaturated acids, and amino acids. A general and direct route for the synthesis of amides is described. The reaction involves the copper-catalyzed amidation of acids, wherein various formamides and an acetamide are used as the amine source. Importantly, this method represents a new strategy for the direct use of acids in the synthesis of amides. DABCO = 1,4-diazabicyclo[2.2.2]octane, TBHP = tert-butyl hydroperoxide. Copyright
- Xie, Ye-Xiang,Song, Ren-Jie,Yang, Xu-Heng,Xiang, Jian-Nan,Li, Jin-Heng
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p. 5737 - 5742
(2013/09/12)
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- NEW CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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Page/Page column 78
(2012/01/14)
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- NEW SELECTIVE CCR2 ANTAGONISTS
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The present invention relates to novel and selective antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD as well as pain.
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Page/Page column 83
(2013/02/28)
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- A novel method for the one-pot conversion of carboxylic acids to N,N-dimethylamides
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A simple, efficient, and new method has been developed for the preparation of N,N-dimethylamides from carboxylic acids. As described below, treatment of a variety of aromatic carboxylic acids with N,N-dimethylsulfamoyl imidazole or N,N-dimethylsulfamoyl chloride in the presence of a mixture of methanesulfonic acid/phosphorus pentoxide (2:1, v/w) proceeded effectively to afford the corresponding N,N-dimethylamides inmoderate to good yields. Thismethod is easy, rapid, and good yielding for the synthesis of N,N-dimethylamides from carboxylic acids. Iranian Chemical Society 2012.
- Kaboudin, Babak,Haghighat, Hamideh
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p. 951 - 955
(2013/02/23)
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- Direct amidation of alcohols with N-substituted formamides under transition-metal-free conditions
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Go tandem! The first example of the direct amidation of alcohols with N-substituted formamides has been developed. A series of tertiary amides, including the challenging N,N-dimethyl-substituted amides, were obtained in moderate to good yields under transition-metal-free conditions (see scheme). TBHP=tert-butyl hydroperoxide. Copyright
- Xu, Kun,Hu, Yanbin,Zhang, Sheng,Zha, Zhenggen,Wang, Zhiyong
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supporting information; experimental part
p. 9793 - 9797
(2012/09/05)
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- Metal-free n-Bu4NI-catalyzed direct synthesis of amides from alcohols and N,N-disubstituted formamides
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A facile and efficient protocol for the synthesis of amides has been developed in the absence of transition metals. The reaction was performed with a catalytic amount of n-Bu4NI and aqueous TBHP as an oxidant. Various alcohols with N,N-disubstituted formamides were examined to furnish the desired products in good yields.
- Li, Huamin,Xie, Jin,Xue, Qicai,Cheng, Yixiang,Zhu, Chengjian
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supporting information
p. 6479 - 6482,4
(2012/12/12)
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- Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium
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Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4701 - 4709
(2012/07/28)
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- Preparation of N,N-dimethyl aromatic amides from aromatic aldehydes with dimethylamine and iodine reagents
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Various N,N-dimethyl aromatic amides were obtained in good to moderate yields by the reaction of aromatic aldehydes with aqueous dimethylamine in the presence of molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature. Under the same conditions and using the same procedure, treatment of aromatic aldehydes and morpholine in the presence of DIH also provided the corresponding N-aroyl morpholines in good to moderate yields. Georg Thieme Verlag Stuttgart · New York.
- Baba, Haruka,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 1175 - 1180
(2012/06/04)
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- Cross coupling of acyl and aminyl radicals: Direct synthesis of amides catalyzed by Bu4NI with TBHP as an oxidant
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A radical solution: A Bu4NI/tert-butyl hydroperoxide (TBHP) catalyzed synthesis of amides through a cross-coupling reaction between acyl and aminyl radicals is described. This method involves the combination of aldehyde C-H bond functionalization and decarbonylation of N,N-disubstituted formamides (see scheme). The cross-coupling is metal-free, has a wide substrate scope, operational simplicity, and gives high yields on scale-up. Copyright
- Liu, Zhaojun,Zhang, Jie,Chen, Shulin,Shi, Erbo,Xu, Yuan,Wan, Xiaobing
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experimental part
p. 3231 - 3235
(2012/05/05)
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- CCR2 RECEPTOR ANTAGONISTS
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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Page/Page column 87
(2011/12/14)
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- Utility of dysprosium as a reductant in coupling reactions of acyl chlorides: The synthesis of amides and diaryl-substituted acetylenes
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Reduction of acyl chlorides with dysprosium metal has been studied. The reducing ability of dysprosium metal is solvent-dependent. Dysprosium metal, which requires neither any additive nor pretreatment, can promote the cross-coupling of acyl chlorides in DMF or DEF to give amides in good yields. When the reaction was performed in N,N-dimethylacetamide, the reductive self-coupling reaction of aroyl chloride took place smoothly and afforded the diaryl-substituted acetylenes in moderate to good yield.
- Chen, Weifeng,Li, Kebin,Hu, Ziqiang,Wang, Liliang,Lai, Guoqiao,Li, Zhifang
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scheme or table
p. 2026 - 2030
(2011/06/18)
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- Palladium-catalyzed carbon-monoxide-free aminocarbonylation of aryl halides using N-substituted formamides as an amide source
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A carbon-monoxide-free aminocarbonylation of various N-substituted formamides with aryl iodides and aryl bromides using palladium acetate and Xantphos is described. The developed methodology is applicable for a wide range of formamides and aryl halides containing different functional groups furnishing good to excellent yield of the corresponding products. N-substituted formamides are used as an amide source wherein a Vilsmeier-type intermediate plays a major role, thus eliminating the need of toxic carbon monoxide gas.
- Sawant, Dinesh N.,Wagh, Yogesh S.,Bhatte, Kushal D.,Bhanage, Bhalchandra M.
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supporting information; experimental part
p. 5489 - 5494
(2011/08/09)
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- Catalytic transamidation reactions compatible with tertiary amide metathesis under ambient conditions
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The carbon-nitrogen bond of carboxamides is extremely stable under most conditions. The present study reveals that simple zirconium- and hafnium-amido complexes are highly efficient catalysts for equilibrium-controlled transamidation reactions between sec
- Stephenson, Nickeisha A.,Zhu, Jiang,Gellman, Samuel H.,Stahl, Shannon S.
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experimental part
p. 10003 - 10008
(2009/12/08)
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- Aminocarbonylation of aryl halides using a nickel phosphite catalytic system
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(Formula Presented) The nickel and phosphite catalytic system with sodium methoxide enables a very efficient aminocarbonylation reaction to be performed between aryl iodides or bromides and N,N-dimethylformamide (DMF). Phosphite ligand 1, which is very st
- Ju, Jinhun,Jeong, Miso,Moon, Jeongju,Hyun, Min Jung,Lee, Sunwoo
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p. 4615 - 4618
(2008/03/13)
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- One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent
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A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2,2-dimethyl-1-propanol resulted with excellent yields.
- Kangani, Cyrous O.,Kelley, David E.
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p. 8917 - 8920
(2007/10/03)
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- NOVEL BENSOPHENONE DERIVATIVES OR SALTS THEREOF
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A benzophenone derivative represented by the following formula: whereinR1 represents, for example, an optionally substituted heterocyclic group, or a substituted phenyl group; Z represents, for example, an alkylene group; R2 represents, for example, a carboxyl group optionally protected with alkyl;R3 represents, for example, an optionally protected hydroxyl group; R4 represents, for example, an optionally substituted cycloalkyloxy group; and R5 represents, for example, a hydrogen atom, ???or a salt thereof has anti-arthritic activity, inhibits bone destruction caused by arthritis, and provides high safety and excellent pharmacokinetics and thus is useful as therapeutic agent for arthritis. These compounds have inhibitory effect on AP-1 activity and are useful as preventive or therapeutic agent for diseases in which excessive expression of AP-1 is involved.
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