- Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
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We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.
- Cheng, Fei,Chen, Tao,Huang, Yin-Qiu,Li, Jia-Wei,Zhou, Chen,Xiao, Xiao,Chen, Fen-Er
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p. 115 - 120
(2022/01/04)
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- Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides
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N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between
- Bhunia, Subhajit,De, Subhadip,Ma, Dawei
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supporting information
(2022/02/09)
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- Synthesis of oxalamides by acceptorless dehydrogenative coupling of ethylene glycol and amines and the reverse hydrogenation catalyzed by ruthenium
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A sustainable, new synthesis of oxalamides, by acceptorless dehydrogenative coupling of ethylene glycol with amines, generating H2, homogeneously catalyzed by a ruthenium pincer complex, is presented. The reverse hydrogenation reaction is also accomplished using the same catalyst. A plausible reaction mechanism is proposed based on stoichiometric reactions, NMR studies, X-ray crystallography as well as observation of plausible intermediates.
- Ben-David, Yehoshoa,Diskin-Posner, Yael,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan
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p. 7188 - 7193
(2020/07/23)
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- Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
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A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.
- Chen, Zhixiang,Jiang, Yongwen,Zhang, Li,Guo, Yinlong,Ma, Dawei
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supporting information
p. 3541 - 3549
(2019/02/26)
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- Cu/ N, N′-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines
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N,N′-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For
- Chen, Zhixiang,Ma, Dawei
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supporting information
p. 6874 - 6878
(2019/09/07)
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- Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones
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The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2/KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.
- Mancuso, Raffaella,Raut, Dnyaneshwar S.,Della Ca, Nicola,Fini, Francesco,Carfagna, Carla,Gabriele, Bartolo
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p. 2204 - 2211
(2015/07/15)
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- CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines
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A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K3PO4 as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N′-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency.
- Zhou, Wei,Fan, Mengyang,Yin, Junli,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 11942 - 11945
(2015/10/06)
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- Recyclization of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile by benzylamine, phenethylamine, and phenylhydrazine
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Reaction of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile with benzylamine, phenethylamine and phenylhydrazine results in the new substituted 5-amino-2,3-dihydro-1H-imidazol-2-ones.
- Chumachenko,Shablykin,Vasilenko,Brovarets
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p. 1710 - 1715
(2013/11/19)
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- Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives
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A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2- dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4- dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.
- Vydzhak,Panchishin, S. Ya.
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experimental part
p. 2391 - 2397
(2009/05/30)
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- Selective and environmentally friendly methodologies based on the use of electrochemistry for fine chemical preparation: An efficient synthesis of N,N′-disubstituted ureas
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A novel efficient synthesis of N,N′-disubstituted ureas has been developed. Aromatic and aliphatic primary amines undergo oxidative carbonylation under atmospheric pressure of carbon monoxide using Pd(II) catalyst in combination with its anodic recycling at a graphite electrode.
- Chiarotto, Isabella,Feroci, Marta
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p. 7137 - 7139
(2007/10/03)
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- Novel acyclic ligands. 3. The syntheses of some amino amides derived from amino acids
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The syntheses of variously protected amino amides derived from the reaction of oxalic esters with ethylenediamine and with the amino acids glycine, L-valine, and L-lysine are described in this paper. The products are potential contrast agents in magnetic resonance imaging (MRI).
- Elsworth, John F.,Msimang, Lorenzo N.,Jackson, Graham E.
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- Purines, Pyrimidines, and Imidazoles. Part 64. Alkylation and Acylation of Some Aminoimidazoles Related to Intermediates in Purine Nucleotide de novo and Thiamine Biosynthesis
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Treatment of ethyl-5-amino-1-benzylimidazole-4-carboxylate with butyl-lithium and methyl iodide gave the 5-N-methylamino derivative (4b) and the 3-methiodide (5) whereas ethyl-5-amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxylate gave both the 5-N-methylamino (6b) and 2-methyl (6d) derivatives.Ethyl 5-amino-1-benzylimidazole-4-carboxylate with acetic anhydride or acetyl chloride gave various products, according to the conditions, including the 5-N-mono- and -N,N-di-acetylamino derivatives (4d) and (4c), respectively, and N,N'-dibenzyloxamide (9).The oxamide also arose from treatment of the imidazole (4a) with formaldehyde. 3-Cyanopropanimidate with ethyl α-amino-α-cyano acetate followed by benzylamine or 2,3-O-isopropylidene-D-ribosylamine afforded ethyl 5-amino-1-benzyl-2-(2-cyanoethyl)imidazole-4-carboxylate and ethyl 5-amino-1-(2,3-O-isopropylidene-α- and β-D-ribofuranosyl)imidazole-4-carboxylates, respectively.Ethyl 5-amino-(2,3-O-isopropylidene-β-D-ribofuranosyl)-2-ethoxycarbonylethylimidazole-4-carboxylate and the corresponding 2-ethoxyethyl nucleoside (6i) were similarly prepared.Oxidation of ethyl 5-amino-2-methylimidazole-4-carboxylate with N-chlorosuccinimide and potassium hydroxide led to ethyl 5-amino-1-benzyl-2-formylimidazole-4-carboxylate and oxidation of the protected 2-ethoxycarbonylethyl nucleoside (6j) with selenium dioxide produced the urea derivative (6l).
- Mackenzie, Grahame,Wilson, Hilary A.,Shaw, Gordon,Ewing, David
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p. 2541 - 2546
(2007/10/02)
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- NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CORRESPONDING OXO-DERIVATIVES USING A PEROXY-SULFUR INTERMEDIATE GENERATED FROM 2-NITROBENZENESULFONYL CHLORIDE AND SUPEROXIDE ANION.
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Thiocarbonyl compounds such as substituted-thioureas, -thioamides, and -thiocarbamates were found to react with a peroxysulfur intermediate (3) which is generated by the treatment of 2-nitrobenzenesulfonyl chloride with potassium superoxide to convert into the corresponding carbonyl compounds in quantitative yield at -30 oC in acetonitrile.
- Kim, Yong Hae,Chung, Bong Chul,Chang, Hae Sung
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p. 1079 - 1082
(2007/10/02)
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- THE REMARKABLY FACILE REARRANGEMENT OF A 2,3,5,6-TETRAKETOPIPERAZINE TO 4,5-DIOXOIMIDAZOLIDINE-2-CARBOXYLIC ACID DERIVATIVES AND ITS REVERSAL
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Reaction of N,N'-dibenzyl-2,3,5,6-piperazinetetraone (1) with boiling ethanol gives ethyl N,N'-dibenzyl-4,5-dioxoimidazolidine-2-carboxylate (2a).Analogous rearrangement products are formed with methyl, n-propyl, n-butyl, and isopropyl alcohols, and ethyl
- Hoare, John H.,Yates, Peter
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p. 281 - 284
(2007/10/02)
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- SYNTHESE DE TRIOXO-2,4,5-DIAZA-1,3-PHOSPHOLIDINES-2-TRISUBSTITUTEES ET REACTIONS AVEC LES ALCOOLS ET LES AMINES
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The 2,4,5-trioxo-1,3-diaza-2-phospholidene trisubstituted, 3, are synthetized in the absence of any base, by the reaction of oxalyle chloride on the primary phosphordiamides 1.The 3 cycles are opened with a Formel bond cleavage in the presence of alcohols and a Formel one in the presence of amines.It can be assumed from the results that Formel pentacoordinate X complex is formed, whose breakdown in the case of amines is slower than the attack on one or the other of the carbonyles.
- Mulliez, M.
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