709-63-7Relevant academic research and scientific papers
Synthesis of a series of new ruthenium organometallic complexes derived from pyridine-imine ligands and their catalytic activity in oxidation of secondary alcohols
Hao, Zhiqiang,Li, Ying,Li, Chen,Wu, Ruitao,Ma, Zhihong,Li, Suzhen,Han, Zhangang,Zheng, Xuezhong,Lin, Jin
, (2019)
Reactions of pyridine imines [C5H4N-2-C(H)?=?N-C6H4-R] [R?=?H (1), CH3 (2), OMe (3), CF3 (4), Cl (5), Br (6)] with Ru3(CO)12 in refluxing toluene gave the corresponding dinuclear ruthenium carbonyl complexes of the type {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) [R?=?H (7); CH3 (8); OMe (9); CF3 (10); Cl (11); Br (12)]. All six novel complexes were separated by chromatography, and fully characterized by elemental analysis, IR, NMR spectroscopy. Molecular structures of 7, 10, 11, and 12 were determined by X-ray crystal diffraction. Further, the catalytic performance of these complexes was also tested. The combination of {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) and NMO afforded an efficient catalytic system for the oxidation of a variety secondary alcohols.
Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy
Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 1372 - 1377 (2022/02/23)
A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.
Synthesis and Catalytic Applications of Multinuclear Gold(I)-1,2,3-Triazolylidene Complexes
Rendón-Nava, David,álvarez-Hernández, Alejandro,Mendoza-Espinosa, Daniel
supporting information, p. 840 - 847 (2021/02/26)
A series of mono- to trinuclear gold(I) complexes (1–3) supported by oxo-functionalized 1,2,3-triazolylidenes have been prepared. All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and in the case of complexes 1 and 2 by x-ray diffraction. The catalytic performance of the new triazolylidene gold complexes was tested in several hydroelementation and cyclization processes employing a variety of alkynes as starting materials. According to the overall results, the trinuclear complex 3 displayed the highest catalytic activity in all processes, providing good to excellent yields under mild reaction conditions.
One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines
Mathew, Sam,Renn, Dominik,Rueping, Magnus,Sagadevan, Arunachalam
, p. 12565 - 12569 (2021/10/21)
A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, withee> 99%.
Catalytic Aerobic Oxidation of Alkenes with Ferric Boroperoxo Porphyrin Complex; Reduction of Oxygen by Iron Porphyrin
Kimura, Kento,Kurahashi, Takuya,Matsubara, Seijiro,Murano, Shunpei
supporting information, p. 2493 - 2497 (2021/12/29)
We herein describe the development of a mild and selective catalytic aerobic oxidation process of olefins. This catalytic aerobic oxidation reaction was designed based on experimental and spectroscopic evidence assessing the reduction of atmospheric oxygen using a ferric porphyrin complex and pinacolborane to form a ferric boroperoxo porphyrin complex as an oxidizing species. The ferric boroperoxo porphyrin complex can be utilized as an in-situ generated intermediate in the catalytic aerobic oxidation of alkenes under ambient conditions to form oxidation products that differ from those obtained using previously reported ferric porphyrin catalysis. Moreover, the mild reaction conditions allow chemoselective oxidation to be achieved.
Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water
Du, Dongdong,Luo, Junfei,Shi, Sanshan,Xie, Pan,Xue, Cheng
, p. 5936 - 5943 (2021/08/23)
With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.
Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion
Bu, Hongzhong,Gu, Jiefan,Li, Yufeng,Ma, Hongfei,Wan, Yuting,Wu, Zheng-Guang,Zhang, Weijian,Zhou, Ying'ao,Zhu, Hongjun
, (2021/07/16)
A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.
Robust Photocatalytic Method Using Ethylene-Bridged Flavinium Salts for the Aerobic Oxidation of Unactivated Benzylic Substrates
Pokluda, Adam,Anwar, Zubair,Boguschová, Veronika,Anusiewicz, Iwona,Skurski, Piotr,Sikorski, Marek,Cibulka, Radek
supporting information, p. 4371 - 4379 (2021/04/02)
7,8-Dimethoxy-3-methyl-1,10-ethylenealloxazinium chloride (1a) was found to be a superior photooxidation catalyst among substituted ethylene-bridged flavinium salts (R=7,8-diMeO, 7,8-OCH2O-, 7,8-diMe, H, 7,8-diCl, 7-CF3 and 8-CF3). Selection was carried out based on structure vs catalytic activity and properties relationship investigations. Flavinium salt 1a proved to be robust enough for practical applications in benzylic oxidations/oxygenations, which was demonstrated using a series of substrates with high oxidation potential, i. e., 1-phenylethanol, ethylbenzene, diphenylmethane and diphenylmethanol derivatives substituted with electron-withdrawing groups (Cl or CF3). The unique capabilities of 1a can be attributed to its high photostability and participation via a relatively long-lived singlet excited state, which was confirmed using spectroscopic studies, electrochemical measurements and TD-DFT calculations. This allows the maximum use of the oxidation power of 1a, which is given by its singlet excited state reduction potential of +2.4 V. 7,8-Dichloro-3-methyl-1,10-ethylenealloxazinium chloride (1 h) can be used as an alternative photocatalyst for even more difficult substrates. (Figure presented.).
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
An Artificial Light-Harvesting System with Tunable Fluorescence Color in Aqueous Sodium Dodecyl Sulfonate Micellar Systems for Photochemical Catalysis
Li, Xinglong,Wang, Ying,Song, Ao,Zhang, Minghui,Chen, Mengning,Jiang, Man,Yu, Shengsheng,Wang, Rongzhou,Xing, Lingbao
supporting information, p. 2725 - 2730 (2021/08/03)
In the present work, an artificial light-harvesting system with fluorescence resonance energy transfer (FRET) is successfully fabricated in aqueous sodium dodecyl sulfonate (SDS) micellar systems. Since the tight and orderly arrangement of dodecyl in the SDS micelles is hydrophobic, tetra-(4-pyridylphenyl)ethylene (4PyTPE) can be easily encapsulated into the hydrophobic layer of SDS micelles through noncovalent interaction, which exhibits aggregation-induced emission (AIE) phenomenon and can be used as energy donor. By using amphoteric sulforhodamine 101 (SR101) fluorescent dye attached to the negatively charged surface of SDS micelles through electrostatic interaction as energy acceptor, the light-harvesting FRET process can be efficiently simulated. Through the steady-state emission spectra analysis in the micelle-mediated energy transfer from 4PyTPE to SR101, the fluorescence emission can be tuned and white light emission with CIE coordinates of (0.31, 0.29) can be successfully achieved by tuning the donor/acceptor ratio. More importantly, to better mimic natural photosynthesis, the SDS micelles with 4PyTPE and SR101 FRET system showed enhanced catalytic activity in photochemical catalysis for dehalogenation of α-bromoacetophenone in aqueous solution and the photocatalytic reaction could be extended to gram levels.
