63829-20-9Relevant academic research and scientific papers
Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O2 as Sole Oxidant
Wang, Xu,Huang, Yubing,Xu, Yanli,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
, p. 2211 - 2218 (2017/02/26)
An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C-N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium intermediate was detected by ESI-MS.
Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds
Yayla, Hatice G.,Wang, Huaiju,Tarantino, Kyle T.,Orbe, Hudson S.,Knowles, Robert R.
, p. 10794 - 10797 (2016/09/09)
We report a new photocatalytic protocol for the redox-neutral isomerization of cyclic alcohols to linear ketones via C-C bond scission. Mechanistic studies demonstrate that key alkoxy radical intermediates in this reaction are generated via the direct homolytic activation of alcohol O-H bonds in an unusual intramolecular PCET process, wherein the electron travels to a proximal radical cation in concert with proton transfer to a weak Br?nsted base. Effective bond strength considerations are shown to accurately forecast the feasibility of alkoxy radical generation with a given oxidant/base pair.
Friedel–Crafts reactions of acyl trifluoromethanesulfonates and cyclic acylsulfonium cations generated from acyl fluorides
Raghavendra Rao,Vallée, Yannick
, p. 4442 - 4447 (2016/07/06)
Reactive acyl trifluoromethanesulfonates are formed from the reaction of acyl fluorides with trimethylsilyl trifluoromethanesulfonate (TMSOTf). These electrophiles undergo Friedel–Crafts reactions with electron-rich aromatics at room temperature. When a sulfur atom is present at their γ position, their cyclization to acylsulfonium cations is observed and is followed by a rearrangement leading to benzothiepinones (or dibenzo[b,e]thiepinones) in 40–85% yield.
Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
, p. 1738 - 1742 (2013/03/28)
Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate
Boroujeni, Kaveh Parvanak,Parvanak, Kamran
experimental part, p. 155 - 163 (2012/01/02)
Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.
Hydrothermal synthesis and catalysis of Nb2O5-WO x nanofiber crystal
Okumura, Kazu,Tomiyama, Takuya,Shirakawa, Shuhei,Ishida, Soichiro,Sanada, Takashi,Arao, Masazumi,Niwa, Miki
experimental part, p. 229 - 235 (2011/10/02)
Nb2O5-WOx synthesized by a hydrothermal method having a long nano-crystalline structure with ca. 10 nm diameter exhibited a high catalytic activity in the Friedel-Crafts alkylations and acylations when it was calcined in N2. The Royal Society of Chemistry.
Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
Parvanak Boroujeni, Kaveh
experimental part, p. 621 - 630 (2010/11/04)
Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.
Friedel-Crafts acylation reaction using carboxylic acids as acylating agents
Kawamura, Masato,Cui, Dong-Mei,Shimada, Shigeru
, p. 9201 - 9209 (2007/10/03)
Dehydrative Friedel-Crafts acylation reaction of aromatic compounds with carboxylic acids as acylating agents was investigated in the presence of Lewis acid- or Br?nsted acid-catalyst. Various metal triflates and bis(trifluoromethanesulfonyl)amides showed catalytic activity at high temperature, among which Eu(NTf2)3 proved to be the most effective and efficiently catalyzed the acylation reaction of alkyl- and alkoxybenzenes with aliphatic and aromatic carboxylic acids at 250 °C. Bi(NTf2)3 was more effective than Eu(NTf2)3 at lower temperature, but proved to be hydrolyzed in the presence of a small amount of water to give HNTf2 and [Bi6O4(OH)4(H2O)6](NTf2)6. The structure of the latter compound was confirmed by a single crystal X-ray analysis. Among five Br?nsted acids, HOTf, HNTf2, HCTf3, TsOH, and Nafion SAC-13, HNTf2 has proved to be the most efficient catalyst and more effective than Eu(NTf2)3 for the acylation of p-xylene with heptanoic acid at 220 °C or lower temperature. HNTf2 catalyzed the acylation of anisole with carboxylic acids in high yields in refluxing toluene with azeotropic removal of water.
Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions
Firouzabadi, Habib,Iranpoor, Nasser,Nowrouzi, Farhad
, p. 10843 - 10850 (2007/10/03)
Stable and non-hygroscopic aluminum dodecatungstophosphate (AlPW 12O40), which is prepared easily from cheap and commercially available compounds was found to be an effective catalyst for Friedel-Crafts acylation reactions using carboxylic acids, acetic anhydride and benzoyl chloride in the absence of solvent under mild reaction conditions.
Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalysed by heteropoly salt Cs2.5H0.5PW12O40
Kaur, Jaspal,Kozhevnikov, Ivan V.
, p. 2508 - 2509 (2007/10/03)
Heteropoly salt Cs2.5H0.5PW12O40 is a highly efficient and reusable solid acid catalyst for the liquid-phase acylation of toluene or anisole with C2 - C12 aliphatic carboxylic acids.
