- Amidation of Aldehydes with Amines under Mild Conditions Using Metal-Organic Framework Derived NiO@Ni Mott-Schottky Catalyst
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Here we report a facile method for the synthesis of nickel oxide-nickel (NiO@Ni) Mott-Schottky catalyst employing metal-organic framework (MOF) as the precursor. A direct amidation protocol of aldehydes with amines has been optimized under mild conditions using NiO@Ni Mott-Schottky catalyst and it shows far better catalytic activity than the NiO?Ni nanoparticles prepared from simple Ni2+ salt under similar reaction conditions. The heterogeneous catalyst is robust, recyclable and efficient to provide comparable yield to costly ligand-based homogeneous Ni catalysts. The scope of the reaction protocol has been explored with variably substituted substrates. The reaction initiates by homolytic cleavage of peroxide and proceeds through radical mechanism.
- Goel, Bharat,Vyas, Ved,Tripathi, Nancy,Kumar Singh, Ajit,Menezes, Prashanth W.,Indra, Arindam,Jain, Shreyans K.
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p. 5743 - 5749
(2020/09/09)
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- An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate
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An efficient and inexpensive synthesis of N-substituted amides from the reaction of nitriles with methyl ethers catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter Reaction under solvent-free conditions. A range of methyl ethers (benzyl, sec-alkyl and tert-butyl ethers) were reacted with nitriles to provide the corresponding amides in high–excellent yields.
- Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
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p. 1355 - 1363
(2019/04/30)
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- Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides
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Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.
- Bai, Shao-Tao,Bheeter, Charles B.,Reek, Joost N. H.
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supporting information
p. 13039 - 13043
(2019/07/31)
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- A solid-supported arylboronic acid catalyst for direct amidation
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An efficient heterogeneous amidation catalyst has been prepared by co-polymerisation of styrene, DVB with 4-styreneboronic acid, which shows wide substrate applicability and higher reactivity than the equivalent homogeneous phenylboronic acid, suggesting potential cooperative catalytic effects. The catalyst can be easily recovered and reused; suitable for use in packed bed flow reactors.
- Du, Yihao,Barber, Thomas,Lim, Sol Ee,Rzepa, Henry S.,Baxendale, Ian R.,Whiting, Andrew
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supporting information
p. 2916 - 2919
(2019/03/27)
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- FeCl2·4H2O catalyzed ritter reaction with nitriles and halohydrocarbons
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An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with various halohydrocarbons catalyzed by FeCl2·4H2O is described. FeCl2·4H2O economically efficiently catalyzed the Ritter reaction under solvent-free conditions. A range of halohydrocarbons (benzyl, tert-butyl and sec-alkyl halohydrocarbons) were coupled with nitriles to provide the corresponding amides in high to excellent yields.
- Feng, Cheng-Liang,Yin, Gui-Bo,Yan, Bin,Chen, Jun-Qing,Ji, Min
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p. 345 - 353
(2019/02/12)
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- Nickel-Catalyzed Phosphine Free Direct N-Alkylation of Amides with Alcohols
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Herein, we developed an operational simple, practical, and selective Ni-catalyzed synthesis of secondary amides. Application of renewable alcohols, earth-abundant and nonprecious nickel catalyst facilitates the transformations, releasing water as byproduct. The catalytic system is tolerant to a variety of functional groups including nitrile, allylic ether, and alkene and could be extended to the synthesis of bis-amide, antiemetic drug Tigan, and dopamine D2 receptor antagonist Itopride. Preliminary mechanistic studies revealed the participation of a benzylic C-H bond in the rate-determining step.
- Das, Jagadish,Banerjee, Debasis
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supporting information
p. 3378 - 3384
(2018/03/26)
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- Synthesis of benzamides through direct condensation of carboxylic acids and amines in the presence of diatomite earth@IL/ZrCl4 under ultrasonic irradiation
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A green, rapid, mild and highly efficient pathway for the preparation of benzamide derivatives is reported. The reaction was performed through direct condensation of benzoic acids and amines under ultrasonic irradiation in the presence of Lewis acidic ionic liquid immobilized on diatomite earth (diatomite earth@IL/ZrCl4). A new, highly efficient and green solid acid catalyst was easily prepared via a two-step procedure and used as an effective reusable catalyst. The prepared catalyst provides active sites for the synthesis of benzamides. The advantages of this method are the use of a superior and recoverable catalyst, low reaction times, simple procedure, high-yielding and eco-friendly process and use of ultrasonic irradiation as a green and powerful technology. Since benzamides are used widely in the pharmaceutical, paper and plastic industries, and also as an intermediate product in the synthesis of therapeutic agents, the presented new synthetic methods for this type of compounds can be of considerable importance.
- Ahmadi, Masoumeh,Moradi, Leila,Sadeghzadeh, Masoud
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p. 7873 - 7889
(2018/09/27)
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- Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles
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An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO 4) 3 ·H 2 O is described. Fe(ClO 4) 3 ·H 2 O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.
- Feng, Chengliang,Yan, Bin,Yin, Guibo,Chen, Junqing,Ji, Min
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p. 2257 - 2264
(2018/10/20)
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- Convenient synthesis of amides by Zn(ClO4)2·6H2O catalysed Ritter reaction with nitriles and halohydrocarbons
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A convenient and high yielding procedure for the synthesis of amides by the Ritter reaction of nitriles and halohydrocarbons in the presence of Zn(ClO4)2·6H2O as a highly stable, effective and available catalyst is described.
- Feng, Chengliang,Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
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supporting information
p. 383 - 386
(2018/08/21)
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- Combination of gold and iridium catalysts for the synthesis of N-alkylated amides from nitriles and alcohols
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An alternative and efficient approach for the synthesis of N-alkylated amides from nitriles and alcohols was proposed and accomplished. By the combination of [(IPr)Au(NTf2)] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) and [CpIrCl2]2 (Cp = η5-pentamethylcyclopentadienyl), a series of nitriles were first hydrated to give amides, in which the resulting amides were further N-alkylated with a variety of alcohols as alkylating agents to afford N-alkylated amides with good to excellent yields. Compared with previous methods for the synthesis of N-alkylated amides from nitriles and alcohols as starting materials, this protocol could be accomplished with high atom economy under more environmentally benign conditions.
- Li, Feng,Ma, Juan,Lu, Lei,Bao, Xiaofeng,Tang, Wanying
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p. 1953 - 1960
(2015/04/27)
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- Transformation of Contact-Explosives Primary Amines and Iodine(III) into a Successful Chemical Reaction under Solvent-Free Ball Milling Conditions
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Any synthetic transformation using contact-explosives primary amines and hypervalent iodine(III) (phenyliodine diacetate) in constrained media (extreme conditions) is practically impossible. Herein, we report a method of controlling the explosion into a successful chemical reaction using the acid-salt NaHSO4. As a proof-of-concept, we considered mechanochemical (ball-milling) cross dehydrogenative coupling (CDC) reaction for the amidation of aldehydes via C-H activation. An isothermal titration calorimetric (ITC) study was helpful to understand the enthalpy changes during the reactions before and after addition of NaHSO4.
- Kumarachar, Tapas,Mal, Prasenjit
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p. 3977 - 3985
(2016/01/25)
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- The direct synthesis of N-alkylated amides via a tandem hydration/N-alkylation reaction from nitriles, aldoximes and alcohols
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A novel strategy for the direct synthesis of N-alkylated amides from nitriles, aldoximes and alcohols was proposed and accomplished in the presence of a Cp*Ir complex. This journal is the Partner Organisations 2014.
- Wang, Nana,Zou, Xiaoyuan,Ma, Juan,Li, Feng
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p. 8303 - 8305
(2014/07/22)
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- Design, synthesis, and biological activity of a novel series of human sirtuin-2-selective inhibitors
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Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2- anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of α-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.
- Suzuki, Takayoshi,Khan, Mohammed Naseer Ahmed,Sawada, Hideyuki,Imai, Erika,Itoh, Yukihiro,Yamatsuta, Katsura,Tokuda, Natsuko,Takeuchi, Jun,Seko, Takuya,Nakagawa, Hidehiko,Miyata, Naoki
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experimental part
p. 5760 - 5773
(2012/07/28)
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