- Copper-catalyzed: Ortho -C(sp2)-H amination of benzamides and picolinamides with alkylamines using oxygen as a green oxidant
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A versatile Cu-catalyzed direct ortho-C(sp2)-H amination of benzamides and picolinamides with alkylamines has been achieved. This method employs cheap and eco-friendly copper as a catalyst and oxygen as an oxidant, and also has the advantages of straightf
- Chen, Gong,Huang, Jie,Li, Qiong,Wang, Shui-Bo
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p. 4802 - 4814
(2020/07/13)
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- Copper-Catalyzed Electrophilic Ortho C(sp2)-H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System
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A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, b
- Begam, Hasina Mamataj,Choudhury, Rajarshee,Behera, Ashok,Jana, Ranjan
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supporting information
p. 4651 - 4656
(2019/06/17)
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- A N - (2 - morpholinyl -5 - trifluoromethyl phenyl) -2 - (3 - methylphenoxy) propionamide preparation method (by machine translation)
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The invention discloses a N - (2 - morpholinyl - 5 - trifluoromethyl-phenyl) - 2 - (3 - methylphenoxy) propionamide of the preparation method, comprises the following steps: The invention provides N - (2 - morpholinyl - 5 - trifluoromethyl-phenyl) - 2 -
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Paragraph 0035; 0036; 0037; 0038
(2019/05/15)
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- Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines
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Electrochemical oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chemical oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochemical techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, we report the first examples of copper-catalyzed electrochemical C-H aminations of arenes at room temperature using undivided electrochemical cells, thereby providing a practical solution for the construction of arylamines. The use of n-Bu4NI as a redox mediator is crucial for this transformation. On the basis of mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochemical C-H functionalization reactions using redox mediators.
- Yang, Qi-Liang,Wang, Xiang-Yang,Lu, Jia-Yan,Zhang, Li-Pu,Fang, Ping,Mei, Tian-Sheng
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p. 11487 - 11494
(2018/09/13)
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- Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature
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In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.
- Li, Qiong,Zhang, Shu-Yu,He, Gang,Ai, Zhaoyan,Nack, William A.,Chen, Gong
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supporting information
p. 1764 - 1767
(2014/04/17)
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- Synthesis and evaluation of a series of heterobiarylamides that are centrally penetrant metabotropic glutamate receptor 4 (mGluR4) positive allosteric modulators (PAMs)
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We report the synthesis and evaluation of a series of heterobiaryl amides as positive allosteric modulators of mGluR4. Compounds 9b and 9c showed submicromolar potency at both human and rat mGluR4. In addition, both 9b and 9c were shown to be centrally pe
- Engers, Darren W.,Niswender, Colleen M.,Weaver, C. David,Jadhav, Satyawan,Menon, Usha N.,Zamorano, Rocio,Conn, P. Jeffrey,Lindsley, Craig W.,Hopkins, Corey R.
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supporting information; experimental part
p. 4115 - 4118
(2010/01/16)
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- Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides
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Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.
- Kiselyov, Alexander S.
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p. 2279 - 2282
(2007/10/03)
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- Study of the diastereoisomers formed between (N-alkyl)-pipecolic acid-anilides and 2R,3R-tartaric acid or O,O′-dibenzoyl-2R,3R-tartaric acid. Do the tartaric acids form molecular-complexes, instead of salts during optical resolutions?
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It was found that during the optical resolution of (N-alkyl)-pipecolic acid-anilides by 2R,3R-tartaric acid and O,O′-dibenzoyl-2R,3R-tartaric acid that the precipitated diastereoisomer was not the salt but a diastereoisomeric complex in 8 cases from 13. T
- Nemak, Katalin,Acs, Maria,Jaszay, Zsuzsa M.,Kozma, David,Fogassy, Elemer
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p. 1637 - 1642
(2007/10/03)
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