1079-02-3Relevant articles and documents
-
Erlenmeyer,Lobeck,Epprecht
, p. 793 (1936)
-
Streitwieser,Klein
, p. 2759,2760 (1963)
Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent
Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng
, p. 2645 - 2649 (2019)
The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.
Cobalt-catalyzed electrochemical C–H/N–H functionalization of N-(quinolin-8-yl)benzamide with isocyanides
Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
, p. 2054 - 2058 (2019)
An efficient synthesis of functionalized iminoisoindolinone derivatives has been achieved via a mild electrochemical oxidative C–H/N–H functionalization/intramolecular annulations with isocyanides in undivided cell equipped with a nickel cathode. In the presence of earth abundant cobalt catalyst, versatile iminoisoindolinone derivatives obtained in good yields and in a sustainable manner by using electricity as an oxidant in place of stoichiometric amount of silver and copper salts.
Copper-Promoted Thiolation of C(sp2)–H Bonds Using a 2-Amino Alkylbenzimidazole Directing Group
Liu, Shuang-Liang,Li, Xue-Hong,Shi, Tan-Hao,Yang, Guang-Chao,Wang, Hai-Li,Gong, Jun-Fang,Song, Mao-Ping
, p. 2280 - 2289 (2017)
A copper-promoted thiolation of C(sp2)–H bonds with disulfides was achieved by using 2-amino alkylbenzimidazole (MBIP amine) as a new and removable N,N-bidentate directing group. This strategy gives a variety of functionalized thioethers in moderate to excellent yields in a simple and efficient way. Importantly, the substrate scope is not limited to aromatic amides; diverse alkenyl amides are also compatible. Furthermore, this synthetic approach provides a potentially feasible way to achieve structural modification of related benzimidazole-containing compounds through direct C–H activation.
Two methods for direct ortho-arylation of benzoic acids
Chiong, Hendrich A.,Pham, Quynh-Nhu,Daugulis, Olafs
, p. 9879 - 9884 (2007)
Two new palladium-catalyzed methods for the direct ortho-arylation of free benzoic acids have been developed. The first method employs stoichiometric silver acetate for iodide removal, aryl iodide as the coupling partner, and acetic acid solvent. This method is applicable to the arylation of electron-rich to moderately electron-poor benzoic acids and tolerates chloride and bromide substituents on both coupling partners. The second method involves the use of aryl chloride, cesium carbonate base, n-butyl-di-1-adamantylphosphine ligand, and DMF solvent and is suitable for both electron-rich and electron-poor benzoic acids. Mechanistic studies of the second method point to the heterolytic C-H bond cleavage as the rate-determining step.
New Pd-phosphorus ylide complexes based on FC60 as heterogeneous nano-catalyst for H/D exchange reaction
Yousefi, Abed,Sabounchei, Seyyed Javad,Hashemi, Ali
, (2021/01/12)
In this account, new Pd(0) complexes of phosphorus ylides based on fullerene C60 (FC60) were synthesized and utilized as the first fullerene-based heterogeneous nano-catalysts for H/D exchange reaction. Four new palladacyclopropa-[60]fullerene complexes 1–4, [(η2-C60)Pd(Y1–4)2] (Y1 = PPh3CHC(O)C6H4-p-NO2, Y2 = PPh3CHC(O)C6H4-p-CH3, Y3 = (p-tolyl)3P-CHC(O)C6H4-p-NO2, and Y4 = (p-tolyl)3P-CHC(O)C6H4-p-CH3), were prepared through dissolving the related α-keto stabilized phosphorus ylide in toluene solution in the presence of FC60 and Pd (dba)2 (dba = dibenzylideneacetone). All of the complexes were characterized using Nuclear magnetic resonance (NMR) (1H, 13C, and 31P), Infrared spectroscopy (IR), Ultraviolet-visible spectroscopy (UV-visible), fluorescence, Electrospray Ionisation Mass Spectrometry (ESI-MS), and Energy-dispersive X-ray spectroscopy (EDX) spectroscopies, and scanning electron microscopy (SEM) and TEM techniques. The data proved that FC60 and two ylides were coordinated to Pd(0) center through two hexagons and two ylidic carbon atoms, respectively. An evaluation was also performed to compare the catalytic activity of synthesized Pd complex 1 and a conventional heterogeneous catalyst, 10% Pd on carbon, in H/D exchange reaction. The results indicate that the process of H/D exchange reaction in aromatic rings of benzoic acid derivatives progressed more efficiently by Pd complex 1.
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian
supporting information, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
