22390-99-4Relevant academic research and scientific papers
Visible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates
Cheng, Li,Dong, Bingbing,Feng, Zengqiang,Li, Yunpu,Wang, Zechao,Wu, Junliang,Zhu, Baoxiang
supporting information, p. 508 - 513 (2021/01/13)
An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones has been described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employs difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones are successfully created via designed systems based on the SET process. The methodology has also provided an operationally simple process with broad functional group compatibility.
Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates
Liu, Qiang,Wang, Rui-Guo,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
supporting information, p. 4391 - 4396 (2020/09/21)
Herein, we report a protocol for visible-light-mediated radical coupling reactions of α-chloroketones and enol acetates to afford 1,4-dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox-catalyzed activation of the α-chloroketone upon photoelectron transfer, carbon–chlorine bond cleavage, and coupling of the resulting radical with the carbon–carbon double bond of the enol acetate. This mild protocol has a wide substrate scope and moderate to good yields. (Figure presented.).
Visible light induced C-H monofluoroalkylation to synthesize 1,4-unsaturated compound
Li, Wei-peng,Zhu, Yu-cheng,Zhou, Yan-jun,Yang, Hong-wei,Zhu, Cheng-jian
, p. 1647 - 1651 (2019/01/22)
We developed a method to synthesize fluorinated 1,4-unsaturated dicarbonyl compounds via photoredox catalyzed radical addition process. Commercially available ethyl bromodifluoroacetate (BrCF2CO2Et) as fluoroalkyl source, the corresponding fluoro-containing dicarbonyl compounds could be obtained in moderate to good yields.
Carboxylic acid addition to terminal alkynes utilizing ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica: A highly reusable and air compatible catalytic system
?ztürk, Bengi ?zgün,Gürcü, Didar,?ehito?lu, Solmaz Karabulut
, p. 11 - 16 (2019/01/24)
In this study, the performance of ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica gel was tested on carboxylic acid addition reactions to terminal alkynes using a variety of carboxylic acid derivatives under air atmosphere. The catalytic system was found to be compatible with air atmosphere and can tolerate even non-degassed solvents. The reaction parameters such as temperature, substrate/catalyst ratio and the effect of carboxylic acid on the selectivity and yield of the reaction were investigated in details. The reaction of arylacetylenes with acetic acid yielded the corresponding E-isomer with conversion values up to 99% with a catalytic loading of 1% Ru. The reusability of the catalyst was tested using acetic acid/benzoic acid and phenylacetylene in toluene at 85 °C under air atmosphere. The catalyst was found to be highly reusable and maintained its activity up to 11th run, reaching a conversion value of 83% with minimum ruthenium leaching.
Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates
Cheng, Pi,Wang, Wei,Wang, Lin,Zeng, Jianguo,Reiser, Oliver,Liang, Yun
, p. 1408 - 1412 (2019/05/06)
Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.
Formation of δ-Lactones with anti-Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates
Geibel, Irina,Dierks, Anna,Müller, Thomas,Christoffers, Jens
, p. 7245 - 7254 (2017/05/31)
The cerium-catalyzed, aerobic coupling of β-oxoesters with enol acetates and dioxygen yields δ-lactones with a 1,4-diketone moiety. In contrast to the Baeyer–Villiger oxidation (BVO), where the higher substituted residue migrates; in the case of this oxid
Direct functionalization of benzylic C-Hs with vinyl acetates via Fe-catalysis
Song, Chun-Xiao,Cai, Gui-Xin,Farrell, Thomas R.,Jiang, Zhong-Ping,Li, Hu,Gan, Liang-Bing,Shi, Zhang-Jie
supporting information; experimental part, p. 6002 - 6004 (2010/11/16)
Direct cross-coupling to construct sp3 C-sp3 C bonds via Fe-catalyzed benzylic C-H activation with 1-aryl vinyl acetate was developed.
Radical-Cations as Intermediates in the Oxidation of Alkenes by Metal Ions
Norman, Julie A.,Thomas, C. Barry,Burrow, Michael J.
, p. 1087 - 1094 (2007/10/02)
The formation of hydroxy acetates in the reaction of some alkenes with lead(IV), cobalt(III), and manganese(III) in acetic acid is demonstrated to involve the intermediacy of alkene radical-cations.A study employing a range of aryl-substituted alkenes has shown that there is an inverse relationship between the yield of hydroxy acetate and the ionisation potential of the organic substrate.The electron deficiency in the radical-cations derived from these alkenes appears to be localised on the double bond: no evidence could be obtained for reaction at the aromatic ring.The introduction of the chlorine atom into this ring had the effect of repressing electron-transfer in cobalt(III) and manganese(III) oxidations but not in those involving lead(IV).
