90-94-8Relevant articles and documents
Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions
Park, Kwihwan,Jiang, Jing,Yamada, Tsuyoshi,Sajiki, Hironao
, p. 1200 - 1205 (2021/12/29)
A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.
Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis
Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan
supporting information, p. 6781 - 6785 (2021/08/20)
A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.
One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy
De Jong, Jorn,Heijnen, Dorus,Helbert, Hugo,Feringa, Ben L.
supporting information, p. 2908 - 2911 (2019/03/17)
A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.
Intramolecular Hydrogen-Bonding Modulates the Nucleophilic Reactivity of Ammonium-Peroxycarboxylates
Mayer, Robert J.,Ofial, Armin R.
supporting information, p. 6010 - 6017 (2018/11/10)
The ammonium-peroxycarboxylic acid mesylates derived from γ-aminobutyric acid, β-alanine, and β-piperidinopropionic acid were synthesized and characterized by spectroscopic methods and X-ray crystallography. To study the nucleophilic reactivities of the corresponding ammonium- and amino-peroxycarboxylates, the kinetics of their reactions with a series of benzhydrylium ions (Ar2CH+) were investigated in alkaline, aqueous solutions at 20 °C. Using sequential-mixing stopped-flow UV/Vis photometry, the rates of the reactions of the short-lived nucleophiles with Ar2CH+ were determined and analyzed by the linear free energy relationship lg k = sN(N + E) furnishing nucleophilicity parameters (N, sN) of the peroxycarboxylates. Quantum chemical calculations indicate that the reactivity of the zwitterionic ammonium-peroxycarboxylates is attenuated by intramolecular N–H···O hydrogen bonding.
A series of BiO: XIy/GO photocatalysts: Synthesis, characterization, activity, and mechanism
Chou, Shang-Yi,Chung, Wen-Hsin,Chen, Li-Wen,Dai, Yong-Ming,Lin, Wan-Yu,Lin, Jia-Hao,Chen, Chiing-Chang
, p. 82743 - 82758 (2016/11/01)
A series of bismuth oxyiodide (BiOxIy)-grafted graphene oxide (GO) sheets with different GO contents were synthesized through a simple hydrothermal method. This is the first report where four composites of BiOI/GO, Bi4O5I2/GO, Bi7O9I3/GO, and Bi5O7I/GO have been characterized using X-ray diffraction, transmission electron microscopy, scanning electron microscopy energy-dispersive spectroscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and diffuse reflectance spectroscopy. The assembled BiOxIy/GO composites exhibited excellent photocatalytic activities in the degradation of crystal violet (CV) under visible light irradiation. The order of rate constants was as follows: Bi7O9I3/GO > Bi4O5I2/GO > Bi4O5I2 > Bi7O9I3 > Bi5O7I/GO > BiOI/GO > BiOI > Bi5O7I > GO. The photocatalytic activity of the Bi7O9I3/GO (or Bi4O5I2/GO) composite reached a maximum rate constant of 0.351 (or 0.322) h-1, which was 1.8 (or 1.7) times higher than that of Bi7O9I3 (or Bi4O5I2), 6-7 times higher than that of BiOI/GO, and 119-130 times higher than that of BiOI. The quenching effects of different scavengers and electron paramagnetic resonance demonstrated that the superoxide radical (O2-) played a major role and holes (h+) and hydroxyl radicals (OH) played a minor role as active species in the degradation of crystal violet (CV) and salicylic acid (SA). Possible photodegradation mechanisms are proposed and discussed in this research.
Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
supporting information, p. 714 - 718 (2015/03/18)
The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
Imidazo[1,5-a]pyridine-1-ylalkylalcohols: Synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures
Murai, Toshiaki,Nagaya, Eri,Shibahara, Fumitoshi,Maruyama, Toshifumi
scheme or table, p. 4943 - 4953 (2012/07/28)
Iodine-mediated cyclization of N-thioacyl 1,2-aminoalcohols derived from aromatic aldehydes and ketones mainly produced bis(1-imidazo[1,5-a]pyridyl) arylmethanes, whereas the reaction of N-thioacyl 1,2-aminoalcohols derived from aliphatic aldehydes and N-thioacyl 1,2-aminoalcohols protected with a silyl group with iodine gave imidazo[1,5-a]pyridine-1-ylalkylalcohols as a major product.
(N-Heterocyclic Carbene)-Pd-catalyzed anaerobic oxidation of secondary alcohols and domino oxidation-arylation reactions
Landers, Brant,Berini, Christophe,Wang, Chao,Navarro, Oscar
experimental part, p. 1390 - 1397 (2011/05/02)
The use of commercially available (SIPr)Pd(cinnamyl)Cl (SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) as a precatalyst for the anaerobic oxidation of secondary alcohols is described. The use of this complex allows for a drastic reduction in the reaction times and catalyst loading when compared to the unsaturated counterpart. This catalytic system is compatible with the use of microwave dielectric heating, decreasing even further catalyst loading and reaction times. Domino Pd-catalyzed oxidation-arylation reactions of secondary alcohols are also presented.(Figure Presented)
Rapid and selective catalytic oxidation of secondary alcohols at room temperature by using (N-Heterocyclic Carbene)-Ni0 systems
Berini, Christophe,Winkelmann, Ole H.,Otten, Jennifer,Vicic, David A.,Navarro, Oscar
supporting information; experimental part, p. 6857 - 6860 (2010/08/03)
The selective, anaerobic catalytic oxidation of secondary alcohols at room temperature by using an in situ (N-heterocyclic carbene)-Ni0 system is presented. The use of non-anhydrous, non-degassed 2,4-dichlorotoluene as both the oxidant and the solvent allows for very short reaction times and very high yields. In addition, a well-defined (N-heterocyclic carbene)-Ni0 complex was synthesized and applied to these oxidation reactions.
Homogeneous, anaerobic (N-heterocyclic carbene)-Pd or -Ni catalyzed oxidation of secondary alcohols at mild temperatures
Berini, Christophe,Brayton, Daniel F.,Mocka, Corey,Navarro, Oscar
supporting information; experimental part, p. 4244 - 4247 (2009/12/31)
The use of aryl chlorides as oxidants for the selective oxidation of a variety of secondary alcohols in anaerobic conditions with (NHC)-Pd and -Ni systems (NHC = N-heterocyclic carbene) at very mild temperatures is presented.
