14547-84-3Relevant academic research and scientific papers
Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
supporting information, (2020/12/21)
A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
Aminocarbonylation of N -Containing Heterocycles with Aromatic Amines Using Mo(CO) 6
Mamone, Marius,Aziz, Jessy,Le Bescont, Julie,Piguel, Sandrine
, p. 1521 - 1526 (2018/01/27)
We describe herein the palladium-catalyzed aminocarbonylation of nitrogen-containing heterocycles with aniline derivatives using molybdenum hexacarbonyl as a CO solid source, expanding the scope of the limited examples. This method is compatible with a variety of substitutions on the aniline moiety. The simple reaction conditions include easily available Pd(dppf)Cl 2 catalyst, DBU as base in DMF at 120 °C for 3 hours in sealed tube thereby leading to the isolation of 21 compounds with yields ranging from 18 to 82%. We also show that double aminocarbonylation reactions are possible in satisfactory yields regarding both coupling partners.
Iron catalysis for the synthesis of ligands: Exploring the products of hydrophosphination as ligands in cross-coupling
Espinal-Viguri, Maialen,Mahon, Mary F.,Tyler, Simon N.G.,Webster, Ruth L.
, p. 64 - 69 (2016/12/09)
Catalytic hydrophosphination is a useful technique for the synthesis of phosphines, however, the phosphine products have been little exploited as ligands in catalysis. We have selected three phosphines prepared by iron catalyzed hydrophosphination and used them as ligands in a series of cross-coupling reactions: Heck, Suzuki-Miyaura and Buchwald-Hartwig. Rather than limit the chemistry to simple cross-coupling partners which are almost guaranteed to perform well in these transformations, industrially relevant substrates which are challenging from and electronic and/or steric perspective, along with substrates which contain several heteroatoms, were explored in order to gauge the true potential of these phosphine ligands.
Efficient conversion of acids and esters to amides and transamidation of primary amides using OSU-6
Nammalwar, Baskar,Muddala, Nagendra Prasad,Watts, Field M.,Bunce, Richard A.
, p. 9101 - 9111 (2015/11/09)
OSU-6, an MCM-41 type hexagonal mesoporous silica with strong Bronsted acid properties, has been used to promote the high-yield conversion of carboxylic acids and esters to carboxamides as well as transamidations of primary amides in a one-pot solventless approach. A metal-free heterogeneous catalyst that promotes all of these processes has not been previously reported. OSU-6 enables these transformations to proceed in shorter times and at lower temperatures for a broad range of substrates. An added benefit is that the catalyst can be recycled and reused multiple times without significant loss of activity.
An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides
Fors, Brett P.,Dooleweerdt, Karin,Zeng, Qingle,Buchwald, Stephen L.
experimental part, p. 6576 - 6583 (2011/02/25)
A catalyst based on a new biarylphosphine ligand (3) for the Pd-catalyzed cross-coupling reactions of amides and aryl chlorides is described. This system shows the highest turnover frequencies reported to date for these reactions, especially for aryl chloride substrates bearing an ortho substituent. An array of amides and aryl chlorides were successfully reacted in good to excellent yields.
Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides
Romero,Harrak,Basset,Orúe,Pujol
experimental part, p. 1951 - 1956 (2009/07/11)
Aryl halides and triflates are coupled with primary amides to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a base. The catalyst system performs well for a large number of different substrates at 100-150 °C without solvent, and with low catalyst levels (0.12 mol % Pd). Nicotinamide might be useful as a nitrogen source in the Pd-catalyzed amination reaction.
AN UNUSUAL SYNTHESIS OF NICOTINAMIDES
Harrington, Philip M.
, p. 683 - 687 (2007/10/02)
Reaction of 2,3-pyridinedicarboxylic anhydride (1) with a substituted aniline (2) in acetic acid gave rise to a mixture of two products.These two products were identified as the cyclic imide (4) and nicotinamide (5).A mechanistic scheme consistent with empirical observations is proposed.
POLAROGRAPHIC REDUCTION OF 1-BENZYL-N-(p-X-PHENYL)-3-AMINOCARBONYLPYRIDINIUM SALTS
Krechl, Jiri,Beranova, Sarka,Volkeova, Vera,Volke, Jiri,Kuthan, Josef
, p. 2008 - 2018 (2007/10/02)
The substitution effect of different groups X (N(CH2CH3)2, OH, OCH3, CH3, NHCOCH3, H, Cl, COOCH2CH3 and NO2) on the polarographic behaviour of 3-(N-p-X-phenylaminocarbonyl)pyridines (I),1-benzyl-N-(p-X-phenyl)-3-aminocarbonylpyridinium cations (II) and their respective 1,4-dihydroderivatives (III) has been investigated in anhydrous solution of dimethylformamide with 0.1 mol 1-1 (n-C4H9)4N+PF6- as supporting electrolyte.The half-wave potentials of the reduction wave of I and II, which correspond to the uptake of a single electron (wave B) and to the formation of a primary radical, obey a Hammett correlation in a similar way as it is in the case of 1-benzyl- and 1-phenyl-3-amino-carbonylopyridinium cations substituted at carbon 4 on the benzene nucleus.The slope q?,R in the Hammett plot equals 0.192 V (I) and 0.104 V (II) for anhydrous DMF and compares thus with this slope obtained with the 1-benzyl- and 1-phenyl derivatives in our previous communications.
