1140-14-3Relevant academic research and scientific papers
Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: An efficient route to aryl ketones
Gu, Lijun,Jin, Cheng,Liu, Jiyan
, p. 3733 - 3736 (2015)
A visible-light-catalyzed synthesis of aryl ketones from aryldiazonium salts, CO and (hetero)arenes at room temperature is discovered. This transformation represents an efficient and attractive synthetic utilization of aryl diazonium salts.
Catalysis studies of macroreticular polystyrene cation-exchange resin with terminal perfluoroalkanesulfonic acids
Lin, Zhenghuan,Guan, Chuanjin,Huang, Limei,Wang, Wen,Ling, Qidan,Zhao, Chengxue
, p. 261 - 266 (2013)
Macroreticular p-(ω-sulfonic-perfluoroalkylated) polystyrene (FPS) resin with the advantages of both sulfonic polystyrene (such as macroreticular Amberlyst-15) and perfluoroalkanesulfonic resin (such as superacidic Nafion NR50) has exhibited excellent catalytic selectivity and activity in cyclization of pseudoionone and condensation of indole. In this paper, FPS was characterized by XPS, nitrogen sorption technique, FESEM and Hammett indicator method, and employed as the solid acid catalyst in the esterification, acylation and alkylation reactions. The FPS resin showed better activity than commercial solid acid catalysts (Amberlyst-15 and Nafion NR50) owing to its high surface area and strong acidity close to superacidity.
Photoenolization/nucleophilic addition enables direct access to 3-alkyl-3-hydroxy-indolin-2-ones
Wang, Zhi-Lv,Tang, Li,Zeng, Wei-Mei,He, Yan-Hong,Guan, Zhi
, (2022/03/27)
A light-driven, catalyst- and additive-free photoenolization/nucleophilic addition reaction for the synthesis of 3-benzyl-3-hydroxyindolin-2-ones is presented. In this reaction, 2-methylbenzophenones undergo light-induced enolization process to afford hydroxy-o-quinodimethanes (hydroxy-o-QDMs), which are then immediately captured by the electrophilic isatins. The reaction utilizes green and clean light energy to realize the C–H activation of the inert benzyl position of 2-methylbenzophenones. This method tolerates a wide scope of substrates and provides concise access to a series of novel 3-benzyl-3-hydroxyindolin-2-ones with 60–99% yields.
Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes
Huang, Zheng,Liu, Guixia,Qian, Lu,Tang, Xixia,Wang, Yulei
supporting information, (2022/02/23)
The use of a chiral (NCP)Ir complex as the precatalyst allowed for the discovery of asymmetric transfer hydrogenation of diaryl ketones with ethanol as the hydrogen source and solvent. This reaction was applicable to various ortho-substituted diaryl keontes, affording benzhydrols in good yields and enantioselectivities. This protocol could be carried out in a gram scale under mild reaction conditions. The utility of the catalytic system was highlighted by the synthesis of the key precursor of (S)-neobenodine.
Carbon-wrapped Fe-Ni bimetallic nanoparticle-catalyzed Friedel-Crafts acylation for green synthesis of aromatic ketones
Bao, Shouxin,Hu, Dianwen,Jia, Mingjun,Lei, Zhenyu,Liu, Jingyao,Song, Xiaojing,Sun, Hao,Zhang, Hao,Zhang, Wenxiang,Zhao, Chen
, p. 7943 - 7954 (2021/12/27)
Developing highly efficient and durable eco-friendly heterogeneous catalysts for the Friedel-Crafts acylation (FCA) reaction has been a long-term and significant target, yet remains a great challenge. Herein, a series of Fe-Ni alloy nanoparticles (NPs) encapsulated inside N-doped carbon spheres (FexNi1?x@NC) was rationally fabricated by pyrolyzing the Fe-Ni bimetallic metal-organic frameworks (BMOFs-FexNi1?x) to this end. Various characterization results demonstrated that FeNi alloy NPs (25 nm) covered by a thin carbon shell (5 nm) were uniformly distributed throughout the entire carbon-based composite. A number of oxidized metal species (Fe3+, Ni2+) are present on the surface of the inner bimetallic core, which should be the main source of catalytically active centers of the carbon-wrapped metal NP catalysts. The composition-optimized Fe0.8Ni0.2@NC with relatively higher positive surface charges exhibited the highest catalytic activity and excellent stability for the acylation of aromatic compounds with acyl chlorides. The density functional theory calculations revealed that the catalytic activity of the FexNi1?x@NC catalysts could arise from the electron transfer,i.e., from the outermost layer of the carbon shell to the inner positively charged Fe-based metal NPs, which can lead to a positive charge distribution (by acting as weak Lewis acid sites) on the external surface of the carbon-encapsulated metal NP catalysts. In this case, the external carbon shell can function as ‘chainmail’ to transfer the Lewis acidity (positive charge), and also to protect the inner metal core from the destructive reaction environment, thus resulting in the formation of highly efficient and durable FCA catalysts.
C(acyl)-C(sp2) and C(sp2)-C(sp2) Suzuki-Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes
?akir, Sinem,Karabiyik, Hande,Kavukcu, Serdar Batikan,Rethinam, Senthil,Türkmen, Hayati
, p. 37684 - 37699 (2021/12/09)
Application of N-heterocyclic carbene (NHC) palladium complexes has been successful for the modulation of C-C coupling reactions. For this purpose, a series of azolium salts (1a-f) including benzothiazolium, benzimidazolium, and imidazolium, bearing a CN-substituted benzyl moiety, and their (NHC)2PdBr2 (2a-c) and PEPPSI-type palladium (3b-f) complexes have been systematically prepared to catalyse acylative Suzuki-Miyaura coupling reaction of acyl chlorides with arylboronic acids to form benzophenone derivatives in the presence of potassium carbonate as a base and to catalyse the traditional Suzuki-Miyaura coupling reaction of bromobenzene with arylboronic acids to form biaryls. All the synthesized compounds were fully characterized by Fourier Transform Infrared (FTIR), and 1H and 13C NMR spectroscopies. X-ray diffraction studies on single crystals of 3c, 3e and 3f prove the square planar geometry. Scanning Electron Microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), metal mapping analyses and thermal gravimetric analysis (TGA) were performed to get further insights into the mechanism of the Suzuki-Miyaura cross coupling reactions. Mechanistic studies have revealed that the stability and coordination of the complexes by the CN group are achieved by the removal of pyridine from the complex in catalytic cycles. The presence of the CN group in the (NHC)Pd complexes significantly increased the catalytic activities for both reactions.
Visible light-driven direct synthesis of ketones from aldehydes via C[sbnd]H bond activation using NiCu nanoparticles adorned on carbon nano onions
Heydari, Akbar,Khorsandi, Zahra,Metkazini, S. Fatemeh Mohammadi,Varma, Rajender S.
, (2021/11/09)
An efficient, straightforward and high yield synthetic approach is described for the direct synthesis of diaryl ketones via the C[sbnd]H bond activation of aldehydes using NiCu nanoparticles adorned on carbon nano onions as an efficient heterogeneous catalyst under the irradiation of a mercury-vapor lamp (400 w) via simple workup. This C[sbnd]H bond activation reaction appears simple and convenient with a wide substrate scope in view of its excellent synthesis prowess as illustrated in the preparation of new-approved anti-Alzheimer and anti-HIV medicinal compounds under greener and mild reaction conditions; catalyst could be recycled and reused five times without any loss of catalytic activity.
Decarboxylation with Carbon Monoxide: The Direct Conversion of Carboxylic Acids into Potent Acid Triflate Electrophiles
Kinney, R. Garrison,Arndtsen, Bruce A.
, p. 5085 - 5089 (2019/04/01)
We report a new strategy for the conversion of carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I2 in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic acids without the use of corrosive and reactive Lewis or Bronsted acid additives, and instead from compounds that are readily available, stable, and functional group compatible.
P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
, p. 12337 - 12340 (2017/11/20)
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation
Doan, Tan L. H.,Dao, Thong Q.,Tran, Hai N.,Tran, Phuong H.,Le, Thach N.
supporting information, p. 7875 - 7880 (2016/05/24)
A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles.
