134-84-9Relevant articles and documents
Solvent-free C-benzoylation and N-benzoylation reactions using
Al-Masum, Mohammad,Wai, Maya Chen,Dunnenberger, Henry
, p. 2888 - 2898 (2011)
An ecofriendly and efficient microwave-irradiated solvent-free benzoylation method was developed. The procedure for C-benzoylation used 50 mol% AlCl 3 as a Lewis acid catalyst at 130°C and was completed in 10 min. The isolated yield was between 71% and 100%. N-benzoylation was conducted in a catalyst-free environment at 130°C in 10 min. The isolated yield was between 80% and 100%. Taylor & Francis Group, LLC.
The Most Twisted Acyclic Amides: Structures and Reactivity
Liu, Chengwei,Shi, Shicheng,Liu, Yongmei,Liu, Ruzhang,Lalancette, Roger,Szostak, Roman,Szostak, Michal
, p. 7771 - 7774 (2018)
The synthesis, crystal structures, and reactivity of the most twisted acyclic amides described to date are reported. Substitution at the nitrogen atom in simple benzamides with Ts and acyl or carbamate groups provides a unique way to achieve almost perpendicular twist in N-acyclic amides (= 77°, N = Ac; = 87°, N = Boc). The overlap between the Nlp and CO π? orbital is disrupted due to geometrical constraints around the N-substituents. The perpendicular acyclic twisted amides represent a transition state mimic of cis-trans peptide isomerization thus far only accessible by excessively twisted bridged lactams.
Visible-light-driven selective oxidation of alcohols using a dye-sensitized TiO2-polyoxometalate catalyst
Yang, Xue,Zhao, Hui,Feng, Jifei,Chen, Yanning,Gao, Shuiying,Cao, Rong
, p. 59 - 66 (2017)
This study demonstrated a dye-sensitized TiO2-polyoxometalate system (denoted TiO2-(PW12-TH)8, where PW12?=?PW12O403? and TH?=?thionine) for selective oxidation of alcohols under visible light. The results showed that various substituted alcohols were transformed into their corresponding aldehydes with high selectivity. Due to more efficient electrons transfer, large surface area, and enhanced visible light absorption, the photocatalytic activity of TiO2-(PW12-TH)8 was superior to any other dye-sensitized system reported to date. The response in the photocurrent-time curves over several on/off cycles of intermittent irradiation showed good reproducibility. The photocurrent response of TiO2-(PW12-TH)8 was much higher than that of TiO2/TH (physical mixture of TiO2 and TH), SiO2-(PW12-TH)8 or P25-(PW12-TH)8 (P25?=?Degussa P25), attributed to the more efficient transfer and longer lifetime of photoexcited electrons. This photocatalytic process confirmed that efficient electron transfer during photocatalytic oxidation plays a vital role in determining the reaction conversion and obtaining good selectivity. Electron paramagnetic resonance (EPR) spectra and radical scavenging experiments proved that superoxide radicals and electrons were the main reactive species in the proposed system, the absence of hydroxyl radicals and holes is demonstrated to be the key of high reaction selectivity.
A Simple and Effective Method for Catalytic Oxidation of Alcohols Using the Oxone/Bu4NHSO4 Oxidation System
An, X. Q.,Kang, M.,Ma, H. C.,Yang, Y. X.,Yang, Z. W.,Zeng, W.
, p. 521 - 523 (2020)
Abstract: A simple and efficient procedure is reported for the oxidation of alcohols tocarbonyl compounds with Oxone (potassium peroxymonosulfate) in the presence oftetrabutylammonium hydrogen sulfate as catalyst with excellent conversion andhigh selectivity using chloroform as solvent at room temperature. The efficiencyof several phase-transfer catalysts in the oxidation of benzyl alcohols andbenzydrol was studied. The proposed catalytic system was also evaluated in theoxidation of alcohols in water at room temperature.
Synthesis, characterization and antibacterial effect of diarylmethylamine-based imines
K?se, Muhammet,Ko?er, Ferudun,Onur, Sultan,Tümer, Ferhan
, (2020)
Firstly, starting from benzoic acid the diarylmethanone compound was synthesized. The diarylmethanone was converted to the corresponding oxime and then reduced to the diarylmethylamine compound. Four different imine compounds were obtained from the condensation of the diarylmethylamine compound with four different salicylaldehyde derivatives. Antimicrobial activities against Gram (+) and Gram (?) microorganisms (Staphylococcus aureus, Bacillus cereus as the Gram (+); Escherichia coli and Salmonella typhimurium as the Gram (?); and Candida albicans as the fungi) were investigated.
Hypervalent iodine in synthesis part 39. Palladium-catalyzed carbonylative coupling of iodonium salts and potassium aryltrifluoroborates by carbon monoxide
Xia, Min,Chen, Zhenchu
, p. 400 - 401 (1999)
Diaryl ketones and chalcones are obtained in good yields by palladium- catalyzed carbonylative coupling of diaryliodonium salts and (E)- phenylethenyl(phenyl)iodonium tetrafluoroborates with potassium aryltrifluoroborates in an atmosphere of carbon monoxide under mild conditions.
Chloramine-T-mediated oxidation of benzylic alcohols using indium(III) triflate
Nakahara, Kazuhide,Kitazawa, Chie,Mineno, Tomoko
, p. 801 - 804 (2017)
The efficient oxidation of benzylic alcohols to carbonyl compounds was performed using chloramine-T and a catalytic amount of indium(III) triflate. The primary benzylic alcohols were converted to the corresponding aldehydes in a good yield, and the secondary benzylic alcohols were oxidized to ketones in a high yield. The optimized reaction conditions required 0.3eq of indium(III) triflate and the use of acetonitrile as a solvent.
Direct Formation and Subsequent Substitution of Remote Ketone-Functionalized Organocopper Reagents
Ebert, Greg W.,Klein, Walter R.
, p. 4744 - 4747 (1991)
Remote ketone-functionalized aryl- and alkylcopper reagents have been synthesized by the use of a highly activated form of zero-valent copper. 5-Bromo-2-pentanone and 4-iodobenzophenone undergo oxidative addition with activated copper to form 5-cuprio-2-pentanone and 4-cupriobenzophenone, respectively.These, in turn, can be cross-coupled with alkyl halides to produce the corresponding alkylated ketones and with acid chlorides to form the corresponding diketones.By use of this methodology, a two-step, one-pot synthesis of methyl (E)-9-oxo-2-decenoate and 8-nonen-2-one have been achieved.The former compound is the methyl ester of the "queen substance" of the honey bee, and the latter is part of an "attractant mixture" for cheese mites found in cheddar cheese.These syntheses were accomplished by converting commercially available 6-bromo-2-hexanone to 6-cuprio-2-hexanone followed by cross-coupling with commercially available methyl 4-bromocrotonate and allyl bromide, respectively.
Photo-Catalytic oxidation of benzyl alcohols using oxone in the presence of n-Bu4NBr in water
Wu, Shang,Ma, Hengchang,Yan, Penghua,Wang, Jianqiang,Ding, Juanjuan,Lei, Ziqiang
, p. 424 - 427 (2009)
A simple, mild and efficient method has been developed for the oxidation of alcohols to aldehydes and ketones using Oxone as oxidant catalyzed by n-Bu4NBr at room temperature in water under UV lamp for 1 h. Oxone smoothly oxidizes benzyl alcohol and its derivatives, benzhydrol and its derivatives.
IPr# - highly hindered, broadly applicable N-heterocyclic carbenes
Flach, Carol,Lalancette, Roger,Li, Guangchen,Mendelsohn, Richard,Meng, Guangrong,Szostak, Michal,Szostak, Roman,Zhao, Qun
, p. 10583 - 10589 (2021)
IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) represents the most important NHC (NHC = N-heterocyclic carbene) ligand throughout the field of homogeneous catalysis. Herein, we report the synthesis, catalytic activity, and full structural and electronic characterization of novel, sterically-bulky, easily-accessible NHC ligands based on the hash peralkylation concept, including IPr#, Np# and BIAN-IPr#. The new ligands have been commercialized in collaboration with Millipore Sigma: IPr#HCl, 915653; Np#HCl; 915912; BIAN-IPr#HCl, 916420, enabling broad access of the academic and industrial researchers to new ligands for reaction optimization and screening. In particular, the synthesis of IPr# hinges upon cost-effective, modular alkylation of aniline, an industrial chemical that is available in bulk. The generality of this approach in ligand design is demonstrated through facile synthesis of BIAN-IPr# and Np#, two ligands that differ in steric properties and N-wingtip arrangement. The broad activity in various cross-coupling reactions in an array of N-C, O-C, C-Cl, C-Br, C-S and C-H bond cross-couplings is demonstrated. The evaluation of steric, electron-donating and π-accepting properties as well as coordination chemistry to Au(i), Rh(i) and Pd(ii) is presented. Given the tremendous importance of NHC ligands in homogenous catalysis, we expect that this new class of NHCs will find rapid and widespread application.
