5333-83-5Relevant articles and documents
A lewis acid site-activated reaction in zeolites: Thiophene acylation by butyryl chloride
Isaev,Fripiat
, p. 257 - 263 (1999)
The acylation of thiophene by butyryl chloride has been studied in the liquid phase in the presence of 12 catalysts: HZSM-5, H-mordenite, and HY (ultrastable Y) with various framework Si/Al ratios, various numbers of Bronsted and Lewis sites, and various amounts of nonframework aluminum. The numbers of Bronsted and Lewis acid sites were obtained by FT-IR using chemisorbed ammonia, as described elsewhere. There is a correlation between the initial rates of reaction and the number of Lewis acid sites, whereas there is no correlation between the initial rates and the number of Bronsted sites. The correlation with the number of Lewis sites may be considered significant, since it expands on more than one order of magnitude. Poisoning of the catalyst probably results from the oligomerization on butyryl chloride. No carboxylic acid has been detected in the course of the reaction. No attempt has been made to determine the nature of the poisoning reaction.
Combining electron-neutral building blocks with intramolecular conformational locks affords stable, high-mobility P- and N-channel polymer semiconductors
Huang, Hui,Chen, Zhihua,Ortiz, Rocio Ponce,Newman, Christopher,Usta, Hakan,Lou, Sylvia,Youn, Jangdae,Noh, Yong-Young,Baeg, Kang-Jun,Chen, Lin X.,Facchetti, Antonio,Marks, Tobin
, p. 10966 - 10973 (2012)
Understanding the relationship between molecular/macromolecular architecture and organic thin film transistor (TFT) performance is essential for realizing next-generation high-performance organic electronics. In this regard, planar π-conjugated, electron-neutral (i.e., neither highly electron-rich nor highly electron-deficient) building blocks represent a major goal for polymeric semiconductors, however their realization presents synthetic challenges. Here we report that an easily accessible (minimal synthetic steps), electron-neutral thienyl-vinylene (TVT)-based building block having weak intramolecular S???O conformational locks affords a new class of stable, structurally planar, solution-processable, high-mobility, molecular, and macromolecular semiconductors. The attraction of merging the weak TVT electron richness with supramolecular planarization is evident in the DFT-computed electronic structures, favorable MO energetics, X-ray diffraction-derived molecular structures, experimental lattice coehesion metrics, and excellent TFT performance. TVT-based polymer TFTs exhibit stable carrier mobilities in air as high as 0.5 and 0.05 cm2/V?s (n- and p-type, respectively). All-TVT polymer-based complementary inverter circuitry exhibiting high voltage gains (～50) and ring oscillator circuitry with high fosc(～1.25 kHz) is readily fabricated from these materials by simple inkjet printing.
Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones
Zhang, Kezhuo,Huang, Jiaxin,Zhao, Wanxiang
supporting information, (2022/02/21)
We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.
Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
, (2021/09/28)
The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
Selective Oxidation of Benzylic sp3C-H Bonds using Molecular Oxygen in a Continuous-Flow Microreactor
Ma, Cunfei,Meng, Qingwei,Tang, Xiaofei,Yu, Zongyi,Yun, Lei,Zhao, Jingnan
, p. 1612 - 1618 (2021/07/21)
Selective aerobic oxidation of benzylic sp3 C-H bonds to generate the corresponding ketones was achieved under continuous-flow conditions. The catalysts N-hydroxyphthalimide (NHPI) and tert-butyl nitrite (TBN) as the precursor of the radical under aerobic conditions motivated this process. Flow microreactors operating under optimized conditions enabled this oxidation with higher efficiency and a shortened reaction time of 54 s (total time was 10 min), which was improved 466 times compared with the batch parallel reaction (7.0 h). Notably, the catalyst and solvent recycling (92.6 and 94.5%) and scale-up experiments (0.87 g h-1 in 28 h) demonstrated the practicability of the protocol. The high product selectivity and functional group tolerance of the process allowed the production of ketones in yields of 41.2 to 90.3%. To reveal the versatility and applicability of this protocol, the late-stage modification of an antiepileptic drug to obtain oxcarbazepine was further conducted.
Synthesis and characterization of AlCl3 impregnated molybdenum oxide as heterogeneous nano-catalyst for the Friedel-Crafts acylation reaction in ambient condition
Jadhav, Arvind H.,Chinnappan, Amutha,Hiremath, Vishwanath,Seo, Jeong Gil
, p. 8243 - 8250 (2015/11/27)
Aluminum trichloride (AlCl3) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO4(AlCl2)2 catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO4(AlCl2)2 catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO4(AlCl2)2 catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.
Iodine promoted α-hydroxylation of ketones
Siddaraju, Yogesh,Prabhu, Kandikere Ramaiah
supporting information, p. 6749 - 6753 (2015/06/25)
A novel method for α-hydroxylation of ketones using substoichiometric amount of iodine under metal-free conditions is described. This method has been successfully employed in synthesizing a variety of heterocyclic compounds, which are useful precursors. α-Hydroxylation of diketones and triketones are illustrated. This strategy provides a novel, efficient, mild and inexpensive method for α-hydroxylation of aryl ketones using a sub-stoichiometric amount of molecular iodine.
Palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides leading to alkyl aryl ketones
Liu, Yan,Yao, Bo,Deng, Chen-Liang,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
supporting information; experimental part, p. 2184 - 2187 (2011/06/20)
Chemical equations presented. A new, simple method for selectively synthesizing alkyl aryl ketones has been developed by palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides. In the presence of PdCl2(MeCN)2, TBAB, and ZnO, a variety of aryl iodides underwent an oxidative coupling reaction with tertiary amines and water to afford the corresponding alkyl aryl ketones in moderate to excellent yields. It is noteworthy that this method is the first example of using trialkylamines as the carbonyl sources for constructing alkyl aryl ketone skeletons.
One-step preparation of α-chlorostyrenes
Borate, Hanumant B.,Gaikwad, Abaji G.,Maujan, Suleman R.,Sawargave, Sangmeshwer P.,Kalal, Kamalakar M.
, p. 4869 - 4872 (2008/02/05)
α-Chlorostyrenes were prepared via a one-step method involving Friedel-Crafts reaction of various aromatic substrates with acid chlorides in the presence of a heterogeneous Si-Fe catalyst.
A new and highly efficient water-soluble copper complex for the oxidation of secondary 1-heteroaryl alcohols by tert-butyl hydroperoxide
Boudreau, Josée,Doucette, Mike,Ajjou, Abdelaziz Nait
, p. 1695 - 1698 (2007/10/03)
The water-soluble copper complex generated in situ from CuCl2 and 2,2′-biquinoline-4,4′-dicarboxylic acid dipotassium salt (BQC), has been revealed as a highly efficient and selective catalyst for the oxidation of secondary 1-heteroaryl alcohols to the corresponding heteroaromatic ketones with aqueous tert-butyl hydroperoxide, under mild conditions. The catalytic system is compatible with different heterocycles such as pyridines, pyrroles, indoles, thiophens, furans, thiazoles, and imidazoles.
