- Synthesis and characterization of Pd(II)–vitamin B6 complex supported on magnetic nanoparticle as an efficient and recyclable catalyst system for C–N cross coupling of amides in deep eutectic solvents
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Vitamin B6–Pd(II) immobilized onto magnetic nanoparticles have been successfully prepared and applied for C–Xcross-coupling reactions with aryl halides in green deep eutectic solvents. The results prove that the Fe3O4@vitamin B6–Pd(II) magnetic nanoparticles show high catalyst activity and good stability. It was also revealed that this complex can be recycled up to five times without any significant loss in catalytic activity.
- Bagheri, Sepideh,Pazoki, Farzane,Esfandiary, Naghmeh,Fadaei, Mohammad Mahdi,Heydari, Akbar
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- Copper(II)-Photocatalyzed N-H Alkylation with Alkanes
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We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.
- Donabauer, Karsten,K?nig, Burkhard,Narobe, Rok,Yakubov, Shahboz,Zheng, Yi-Wen
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p. 8582 - 8589
(2020/09/23)
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- Nickel-catalyzed reductive amidation of aryl-triazine ethers
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The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.
- Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
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supporting information
p. 1992 - 1995
(2020/02/22)
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- Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature
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The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.
- Do, Hien-Quang,Bachman, Shoshana,Bissember, Alex C.,Peters, Jonas C.,Fu, Gregory C.
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supporting information
p. 2162 - 2167
(2014/03/21)
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- Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines
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An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.
- Wu, Ji-Wei,Wu, Ya-Dong,Dai, Jian-Jun,Xu, Hua-Jian
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supporting information
p. 2429 - 2436
(2014/09/30)
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- Uptake and localisation of rhenium fac-tricarbonyl polypyridyls in fluorescent cell imaging experiments
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The synthesis of a series of rhenium fac tricarbonyl bisimine complexes and their application as lumophores in fluorescence imaging of yeast and human adenocarcinoma cells is reported. A wide range of complexes are synthesised with varying charges and lip
- Fernandez-Moreira, Vanesa,Thorp-Greenwood, Flora L.,Amoroso, Angelo J.,Cable, Joanne,Court, Jonathan B.,Gray, Victoria,Hayes, Anthony J.,Jenkins, Robert L.,Kariuki, Benson M.,Lloyd, David,Millet, Coralie O.,Williams, Catrin Ff.,Coogan, Michael P.
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scheme or table
p. 3888 - 3901
(2010/09/17)
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- Acid-catalysed N-alkyl heterolysis of tertiary pyridinecarboxamides and benzamides under mild conditions
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Tertiary pyridinecarboxamides 1-9 and related benzamides 10-18 bearing a tert-butyl substituent were found to undergo alkyl-nitrogen heterolysis under unusually mild conditions. Accordingly, the corresponding secondary amides 19-33 have been isolated in high yields as the sole reaction product. Through a kinetic study based on pH-rate profiles and activation parameters, we have shown that the alkyl-nitrogen fission involved an initial protonation of the amide group that would concern the oxygen atom.
- Auzeil, Nicolas,Largeron, Martine,Fleury, Maurice-Bernard
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p. 1703 - 1709
(2007/10/03)
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- Influence of steric crowding on the electrochemical reduction of substituted tertiary pyridylcarboxamides in aqueous acidic medium
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In order to assess the influence of the steric crowding on the electrochemical reduction of pyridycarboxamides, we have studied a series of tertiary aromatic or alicyclic pyridylcarboxamides. We have shown that increasing steric hindrance at the amide nit
- Largeron, Martine,Auzeil, Nicolas,Bacque, Eric,Fleury, Maurice-Bernard
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p. 495 - 501
(2007/10/03)
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