3815-24-5Relevant articles and documents
Electrochemical, ESR and quantum chemical study of 1-substituted naphthalenes and their radical anions
Vasilieva,Irtegova,Vaganova,Shteingarts
, p. 73 - 78 (2008)
Electrochemical reduction and oxidation of a series of 1-substituted naphthalenes (1-X-naphthalenes) have been studied by the method of cyclic voltammetry (CV). The first reduction peak of the majority of these compounds corresponds to a one-electron transfer to form the relatively stable radical anion (RA). For these species, ESR spectra have been registered and interpreted, the life time has been estimated. The first oxidation peaks of 1-X-naphthalenes are irreversible and correspond to a transfer of two or more electrons. Copyright
Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
, (2021/10/05)
We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides
Li, Zhaohui,Liu, Long,Xu, Kaiqiang,Huang, Tianzeng,Li, Xinyi,Song, Bin,Chen, Tieqiao
supporting information, p. 5517 - 5521 (2020/07/14)
A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.
Amidation reaction of carboxylic acid with formamide derivative using SO3?pyridine
Kawano, Shota,Saito, Kodai,Yamada, Tohru
supporting information, p. 584 - 586 (2018/04/12)
The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3?py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.
Palladium-catalyzed directing group-assisted C8-triflation of naphthalenes
Yang, Zhi-Wei,Zhang, Qi,Jiang, Yuan-Ye,Li, Lei,Xiao, Bin,Fu, Yao
supporting information, p. 6709 - 6711 (2016/06/01)
The transition-metal-catalyzed direct triflation of naphthyl amides and naphthyl ketones has been accomplished for the first time. Benzophenone (BP) was found to be a suitable ligand for the cross-coupling reactions. Density functional theory (DFT) calculations revealed that excessive amounts of HOTf inhibit the reductive elimination of the C-F bond to realize the unusual reductive elimination of the C-OTf bond.
Hydride Reduction by a Sodium Hydride-Iodide Composite
Too, Pei Chui,Chan, Guo Hao,Tnay, Ya Lin,Hirao, Hajime,Chiba, Shunsuke
supporting information, p. 3719 - 3723 (2016/03/26)
Sodium hydride (NaH) is widely used as a Br?nsted base in chemical synthesis and reacts with various Br?nsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.
Palladium-Catalyzed Aminocarbonylation of Aryl Halides with 2,4,6-Trichloro-1,3,5-triazine/Formamide Mixed Reagent
Iranpoor, Nasser,Panahi, Farhad,Roozbin, Fatemeh,Erfan, Soodabeh,Rahimi, Sajjad
, p. 1781 - 1787 (2016/04/05)
In this work, the mixture of formamide and 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride or TCT) is introduced as a new amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of a catalytic amount of palladium and TCT/formamide reagent, a range of aryl halides (X = Cl, Br, I) were converted into amides efficiently in N,N-dimethylformamide at 120 °C. The 2,4,6-trichloro-1,3,5-triazine/formamide mixed reagent was found to be an efficient amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of this reagent and a catalytic amount of Pd, a range of amides were synthesized by using aryl halides.
Copper-catalyzed amide bond formation from formamides and carboxylic acids
Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
, p. 11 - 14 (2015/01/30)
A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
Potassium tert-Butoxide-Mediated Amine Acyl Exchange Reaction of N,N-Disubstituted Formamides with Aromatic Carbonyl Derivatives via Sequential C-N Bond Cleavage/Formation: An Approach to Aromatic Amides
Zhang, Ming-Zhong,Guo, Qing-Hu,Sheng, Wen-Bing,Guo, Can-Cheng
, p. 2855 - 2861 (2015/09/28)
A novel potassium tert-butoxide-mediated amine acyl exchange of N,N-disubstituted formamides with aromatic carbonyl derivatives in a sequential C-N bond cleavage/formation process leading to aromatic amides is described. This methodology tolerates a wide range of aromatic carbonyl compounds, including aromatic aldehydes, acyl chlorides, unactivated esters, and acid anhydrides. The usage of inexpensive and readily available reagents, broad substrate scope, and the simple, mild (50°C) and transition metal-free conditions make this protocol very practical. In addition, a plausible reaction mechanism is proposed on the basis of experimental observations.
Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts
Bai, Cuihua,Yao, Xianfang,Li, Yingwei
, p. 884 - 891 (2015/02/19)
A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).
