- 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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- Photoinduced Aerobic Iodoarene-Catalyzed Spirocyclization of N-Oxy-amides to N-Fused Spirolactams**
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Iodoarene catalysis is a powerful methodology that usually requires an excess of oxidant, or of redox mediator if the terminal oxidant is dioxygen, to generate the key hypervalent iodine intermediate to proceed efficiently. We report that, using the spiro-cyclization of amides as a benchmark reaction, aerobic iodoarene catalysis can be enabled by relying on a pyrylium photocatalyst under blue light irradiation. This unprecedented dual organocatalytic system allows the use of low catalytic loading of both catalysts under very mild operating conditions.
- Cariou, Kevin,Habert, Lo?c
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p. 171 - 175
(2020/10/27)
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- Visible-Light Decatungstate/Disulfide Dual Catalysis for the Hydro-Functionalization of Styrenes
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We describe an efficient photoredox system, relying on decatungstate/disulfide catalysts, for the hydrofunctionalization of styrenes. In this methodology the use of disulfide as a cocatalyst was shown to be crucial for the reaction efficiency. This photoredox system was employed for the hydro-carbamoylation, -acylation, -alkylation, and -silylation of styrenes, giving access to a large variety of useful building blocks and high-value molecules such as amides and unsymmetrical ketones from simple starting materials.
- Prieto, Alexis,Taillefer, Marc
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supporting information
p. 1484 - 1488
(2021/03/08)
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- Nickel-catalyzed: C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
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A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamides with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway. This journal is
- Yang, Peng,Wang, Xiuhua,Ma, Yu,Sun, Yaxin,Zhang, Li,Yue, Jieyu,Fu, Kaiyue,Zhou, Jianrong Steve,Tang, Bo
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supporting information
p. 14083 - 14086
(2020/11/20)
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- Direct synthesis of amides from nonactivated carboxylic acids using urea as nitrogen source and Mg(NO3)2or imidazole as catalysts
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A new method for the direct synthesis of primary and secondary amides from carboxylic acids is described using Mg(NO3)2·6H2O or imidazole as a low-cost and readily available catalyst, and urea as a stable, and easy to manipulate nitrogen source. This methodology is particularly useful for the direct synthesis of primary and methyl amides avoiding the use of ammonia and methylamine gas which can be tedious to manipulate. Furthermore, the transformation does not require the employment of coupling or activating agents which are commonly required.
- Blacker, A. John,Chhatwal, A. Rosie,Lomax, Helen V.,Marcé, Patricia,Williams, Jonathan M. J.
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p. 5808 - 5818
(2020/06/21)
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- Primary fatty acid amide preparation method
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The present invention provides a primary fatty acid amide preparation method. According to the present invention, under the action of a single auxiliary agent phosphine-containing transition metal catalyst or a combined auxiliary agent comprising a phosphine-free transition metal catalyst and a phosphine-containing ligand, terminally substituted olefin or cyclo-olefin, carbon monoxide and an ammonium salt are subjected to a hydrogen carboamidation reaction so as to prepare the primary fatty acid amide compound in one step; the raw material and the catalyst of the reaction are inexpensive and easy to obtain, and the synthesis process is simple, such that the synthesis cost is substantially reduced; the preparation method has characteristics of mild reaction condition and high yield, and issuitable for industrial production; and the raw material and the catalyst of the reaction are clean, non-toxic and low environment pollution.
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Paragraph 0200-0202
(2018/10/19)
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- Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride
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Palladium-catalyzed hydroaminocarbonylation of alkenes for the synthesis of primary amides has long been an elusive aim. Here, we report an efficient catalytic system which enables inexpensive NH4Cl to be utilized as a practical alternative to gaseous ammonia for the palladium-catalyzed alkene-hydroaminocarbonylation reaction. Through appropriate choice of the palladium precursors and ligands, either branched or linear primary amides can be obtained in good yields with good to excellent regioselectivities. Primary mechanistic studies were conducted and disclosed that electrophilic acylpalladium species were capable of capturing the NH2-moiety from ammonium salts to form amides in the presence of CO with NMP as a base.
- Gao, Bao,Zhang, Guoying,Zhou, Xibing,Huang, Hanmin
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p. 380 - 386
(2018/01/12)
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- METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY
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Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.
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- Chemoselective hydrogenation of the olefinic bonds using a palladium/magnesium-lanthanum mixed oxide catalyst
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A palladium/magnesium-lanthanum mixed oxide catalyst is found to be an efficient heterogeneous catalyst for the chemoselective hydrogenation of olefinic double bonds in the presence of various functional groups. The catalyst was recovered by centrifugation and reused for several cycles with consistent activity and selectivity. Copyright
- Kantam, Mannepalli Lakshmi,Kishore, Ramineni,Yadav, Jagjit,Sudhakar, Medak,Venugopal, Akula
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supporting information; experimental part
p. 663 - 669
(2012/04/23)
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- Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain
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We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.
- Perez-Medrano, Arturo,Donnelly-Roberts, Diana L.,Honore, Prisca,Hsieh, Gin C.,Namovic, Marian T.,Peddi, Sridhar,Shuai, Qi,Wang, Ying,Faltynek, Connie R.,Jarvis, Michael F.,Carroll, William A.
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scheme or table
p. 3366 - 3376
(2010/04/03)
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- Superacidic activation of α,β-unsaturated amides and their electrophilic reactions
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The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low-temperature NMR) is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Koltunov, Konstantin Yu.,Walspurger, Stephane,Sommer, Jean
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p. 4039 - 4047
(2007/10/03)
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- Rhodium-catalyzed heck-type coupling of boronic acids with activated alkenes in an aqueous emulsion
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Intermolecular couplings between arylboronic acids and activated alkenes catalyzed by a water-soluble tert-bulyl amphosrhodium complex were found to progress at room temperature and generated Heck-type products with high yields and excellent selectivity. Substitution on the alkene component encouraged the formation of products arising from a conjugate addition-protonation process. In the case of Heck product formation, it was necessary to add two equivalents of the alkene component whereby one equivalent is believed to act as a sacrificial hydride acceptor.
- Lautens, Mark,Mancuso, John,Grover, Harpreet
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p. 2006 - 2014
(2007/10/03)
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- A Facile Approach to 2-Arylethylamines via Polymeric Palladium Catalyst
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2-Arylethylamines were synthesized in moderate yields via Heck reaction of acrylamide with iodobenzenes in the presence of polymeric catalyst P-ph-phen.Pd(0) followed by hydrogenation and subsequent Hofmann reaction.
- Zhuangyu, Zhang,Yi, Pan,Hongwen, Hu,Tsi-yu, Kao
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p. 3563 - 3574
(2007/10/02)
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