1020-39-9Relevant academic research and scientific papers
Oxazolidin-2-one-promoted CuI-catalyzed amidation of aryl halides and cyclization of o-halobenzanilides
Heng, Chang Ma,Xuan, Zhen Jiang
, p. 1335 - 1340 (2008)
Oxazolidin-2-one was found to be a versatile and efficient ligand for the CuI-catalyzed amidation of aryl halides and the cyclization of ortho-halobenzanilides. Notably, the less active halides could also be applied successfully in the synthesis of benzoxazoles and benzothiazoles. Georg Thieme Verlag Stuttgart.
Highly selective C-H functionalization/halogenation of acetanilide
Wan, Xiaobing,Ma, Zhongxun,Li, Bijie,Zhang, Keya,Cao, Shaokui,Zhang, Shiwei,Shi, Zhangjie
, p. 7416 - 7417 (2006)
Highly regioselective C-H functionalization/halogenation of acetanilides to produce ortho-haloacetanilides was catalyzed by Pd(OAc)2 and Cu(OAc)2 with CuX2 as the halogen source. Copyright
TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides
Chen, Cui,Liu, Weibing,Zhou, Peng
, p. 2250 - 2255 (2016)
A TBHP-mediated dehydrogenative cross-oxidative-coupling approach has been developed for the synthesis of N-arylbenzamides from methylarenes and acetanilides. This cross-coupling method is free of transition metal catalysts and ligands, and no extra organic solvents are required, which make it an useful and attractive strategy for the straightforward construction of C-N bonds. Besides, this conversion is an important complement to the conventional C-N forming strategies.
Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides
Huang, Fei,Wu, San,Hu, Weiye,Zhang, Songlin
, p. 1090 - 1096 (2018)
A practical and efficient method for N-arylation of benz-amides promoted by potassium carbonate in the presence of DMEDA was developed. The reaction was carried out without addition of any transition-metal catalyst to afford a variety of N-arylated products in moderate to good yields (up to 97%).
Copper catalyzed N-arylation between aryl halides and nitriles in water: An efficient tandem synthesis of benzanilides
Wang, Jichao,Yin, Xinchi,Wu, Jun,Wu, Datong,Pan, Yuanjiang
, p. 10463 - 10469 (2013)
A series of benzanilide compounds were synthesized through copper-catalyzed tandem reactions. With the assistance of ionic liquid as phase transfer catalyst, aryl halides, and nitriles underwent a hydrolysis/coupling pathway to form benzanilides in water. Advantages of this reaction include the use of water as the environmental friendly solvent, short reaction time, and the tolerance of various functional groups. A proposed mechanism based on control experiments is also presented.
Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis
Hering, Thea,Mühldorf, Bernd,Wolf, Robert,K?nig, Burkhard
, p. 5342 - 5345 (2016)
Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O2 as the oxidant. A photocatalytic oxidative chlorination is described based on the organic dye riboflavin tetraacetate mimicking the enzymatic process. The chemical process allows within the suitable arene redox potential window a broader substrate scope compared to the specific activation in the enzymatic binding pocket. Chlorination of arenes with chloride anions: The photochemical analogue of the enzymatic chlorination of Flavin-adenine dinucleotide (FAD)-dependent halogenases is possible in the presence of riboflavin, air, acetic acid, and blue light (see scheme; RFT=riboflavin tetraacetate).
Migration of the Hydroxyl Group of N-Hydroxy-N-phenylamides to the Phenyl Group with Tertiary Phosphines and Tetrachloromethane. A Novel Transhydroxylation Reaction
Kikugawa, Yasuo,Mitsui, Kimiyo
, p. 1369 - 1372 (1993)
The hydroxyl group of N-hydroxyl-N-phenylamides rearranges mainly to the ortho position of the N-phenyl ring by the system (n-Bu)3P-CCl4-CH3CN; use of less than a stoichiometric amount of (n-Bu)3P is effective for this reaction.
Efficient synthesis of amides and esters from alcohols under aerobic ambient conditions catalyzed by a Au/mesoporous Al2O3 nanocatalyst
Chng, Leng Leng,Yang, Jinhua,Ying, Jackie Y.
, p. 1916 - 1925 (2015)
An efficient heterogeneous Au/mesoporous alumina nanocatalyst has been successfully developed for the synthesis of amides and esters from simple building blocks of readily available alcohols and amines. The processes were simple and were performed at room temperature and atmospheric pressure of O2 to form the desired products with up to 97% isolated yield. The ability of Au/mesoporous alumina to catalyze these reactions under ambient conditions further enhances the sustainability of these chemical processes. Furthermore, the nanocatalyst was stable to air and water and could be recovered and reused easily. The enhanced catalytic activity of Au/mesoporous alumina might be attributed to the presence of negatively charged Au nanoparticles that could promote oxidation processes as well as the stability of the mesoporous alumina support calcined at a high temperature of 800°C. Gold for green: Gold nanoparticles supported on mesoporous alumina catalyze the efficient synthesis of amides and esters from simple building blocks of readily available alcohols and amines under ambient aerobic reaction conditions (R1=aryl, alkyl, and R2=H, alkyl).
Pd-Catalyzed Oxidation of Aldimines to Amides
Gao, Shanshan,Ma, Yaorui,Chen, Weidong,Luo, Junfei
, p. 2191 - 2194 (2018)
Methods for the synthesis of amides via the direct oxidation of imines are rarely reported. Here we report an efficient method for Pd-catalyzed oxidation of imines to amide derivatives by the use of cheap aqueous tert -butyl hydroperoxide as an oxidant through a Wacker-type reaction. This method is practically convenient and displays high functional group tolerance, allowing a variety of imines to transform into the corresponding amide derivatives in moderate to good yields.
Iron-catalyzed N-arylations of amides
Correa, Arkaitz,Elmore, Simon,Bolm, Carsten
, p. 3527 - 3529 (2008)
A method was proposed for iron-catalyzed N-arylation of primary amides and its applicability to the synthesis of N-heterocycles by intramolecular ring closures. The method used a catalyst system of 10 mol % of FeCl3 and 20 mol % of N,N'-dimethylethylenediamine (DMEDA). The study found that secondary amides of N-methylbenzamide and N-benzylbenzamide produce N-arylated products in trace amounts. The method developed an iron-based catalyst system for efficient N-arylations of primary amides with aryl iodides. The study used a sealable tube equipped with a magnetic stir bar charged with amide, or K 3PO4, or K2CO3, or FeCl3. The study used NMR spectroscopic analysis to determine the identity and purity of the products. The method observed that different substituted aryl iodides made a positive impact on the reaction.
