104-93-8Relevant articles and documents
Selective Production of Diethyl Maleate via Oxidative Cleavage of Lignin Aromatic Unit
Cai, Zhenping,Long, Jinxing,Li, Yingwen,Ye, Lin,Yin, Biaolin,France, Liam John,Dong, Juncai,Zheng, Lirong,He, Hongyan,Liu, Sijie,Tsang, Shik Chi Edman,Li, Xuehui
, p. 2365 - 2377 (2019)
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Hydrogenation of aromatic aldehydes to aromatic hydrocarbons over Cu-HZSM-5 catalyst
Kong, Xiangjin,Chen, Ligong
, p. 45 - 49 (2014)
With benzaldehyde as a model compound, the hydrogenation of aromatic aldehydes to aromatic hydrocarbons was investigated. Cu-HZSM-5 exhibited excellent catalytic performance for the reaction. The obtained catalysts were characterized by N2 adsorption/desorption, N2O chemisorptions, X-ray diffraction, NH3-temperature programmed desorption and X-ray photoelectron spectroscopy. It was found that Cu 0 active species exhibited poor activity for the hydrogenation of benzene ring, while the strong acidity of HZSM-5 accelerated the hydrogenation reaction via hydrogen spillover phenomenon and the C-O activation effect. In addition, the catalyst was proved to be effective for the hydrogenation of a series of aromatic aldehydes to corresponding aromatic hydrocarbons.
Pd(0)-CATALYZED ELECTRO-REDUCTIVE COUPLING OF ARYL HALIDES
Torii, Sigeru,Tanaka, Hideo,Morisaki, Kazuo
, p. 1655 - 1658 (1985)
An efficient electro-reductive coupling of aryl bromides and iodides into biaryls has been performed by the electrolysis with Pd(0)- and/or Pd(II)-catalysts in a DMF-Et4NOTs-(Pb cathode) system. 4-Bromo- and 2-bromopyridines were also converted into the corresponding bipyridyls, respectively.
Iodothyronine Deiodinase Mimics. Deiodination of o,o'-Diiodophenols by Selenium and Tellurium Reagents
Vasil'ev, Andrei A.,Engman, Lars
, p. 3911 - 3917 (1998)
To better understand, and in the extension mimic, the action of the three selenium-containing iodothyronine deiodinases, o,o'-diiodophenols were reacted under acidic conditions with sodium hydrogen telluride, benzenetellurol, sodium hydrogen selenide, or benzeneselenol and under basic conditions with the corresponding deprotonated reagents. Sodium hydrogen telluride was found to selectively remove one iodine from a variety of 4-substituted o,o'-diiodophenols, including a protected form of thyroxine (T4). Thus, it mimics the D1 variety of the iodothyronine deiodinases. Sodium telluride was a more reactive deiodinating agent toward o,o'-diiodophenols, often causing removal of both halogens. Benzenetellurol and sodium benzenetellurolate sometimes showed useful selectivity for monodeiodination. However, the products were often contaminated by small amounts of organotellurium compounds. Sodium hydrogen selenide, sodium selenide, benzeneselenol, and sodium benzeneselenolate were essentially unreactive toward o,o'-diiodophenols. To gain more insight into thyroxine inner-ring deiodination, substituted 2,6-diiodophenyl methyl ethers were treated with some of the chalcogen reagents. Reactivity and selectivity for monodeiodination varied considerably depending on the substituents attached to the aromatic nucleus. In general, it was possible to find reagents that could bring about the selective mono- or dideiodination of these substrates.
Mo(CO)6-Promoted Reductive Cleavage of the Carbon-Sulfur Bond
Luh, Tien-Yau,Wong, Chi Sang
, p. 5413 - 5415 (1985)
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PALLADIUM-CATALYZED CROSS-COUPLING OF ARYLDIAZONIUM SALTS WITH TETRAMETHYLTIN IN AQUEOUS MEDIUM
Bumagin, N. A.,Sukhomlinova, L. I.,Tolstaya, T. P.,Vanchikov, A. N.,Beletskaya, I. P.
, p. 2419 (1990)
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DESULFURIZATION OF MERCAPTANS TO HYDROCARBONS BY CARBON MONOXIDE AND WATER IN THE PRESENCE OF COBALT CARBONYL
Shim, Sang Chul,Antebi, Shlomo,Alper, Howard
, p. 1935 - 1938 (1985)
Benzylic mercaptans and thiophenols undergo desulfurization when exposed to carbon monoxide and water, with cobalt carbonyl as the catalyst; carbonyl sulfide is evolved in these reactions.
Bromine-induced Photochemical Protodesilylation of Benzyltrimethylsilanes by Hydrogen Bromide
Baciocchi, Enrico,Crescenzi, Manuela,Giacco, Tiziana Del
, p. 3377 - 3378 (1991)
Benzyltrimethylsilanes are efficiently converted into toluenes by a Br2-induced photochemical chain process in the presence of HBr.
Rapid coupling of methyl iodide with aryltributylstannanes mediated by palladium(0) complexes: A general protocol for the synthesis of 11CH3-labeled PET tracers
Suzuki, Masaaki,Doi, Hisashi,Bjoerkman, Margareta,Andersson, Yvonne,Langstroem, Bengt,Watanabe, Yasuyoshi,Noyori, Ryoji
, p. 2039 - 2042 (1997)
The reaction of methyl iodide and (excess) aryltributylstannane to give a methylarene has been studied with the focus on the realization of rapid coupling for incorporation of short-lived radionuclides into bioactive organic compounds. The coupling of methyl iodide with tributylphenylstannane (40 equiv) is accomplished in >90% yield within 5 min at 60°C with a tri-o-tolylphosphine-bound, coordinatively unsaturated Pd(o) complex together with a Cu(I) salt and K2CO3 in DMF. This protocol is applicable to a variety of homo- and heteroaromatic tin compounds, to give the corresponding methylated derivatives. The effects of the tri-o-tolylphosphine ligand, a Cu(I) salt, and DMF are discussed. This new protocol provides a firm chemical basis for the synthesis of 11CH3-incorporated PET tracers.
Diels-Alder reaction of tetraarylcyclopentadienones with benzo[: B] thiophene S, S-dioxides: An unprecedented de-oxygenation vs. sulfur dioxide extrusion
Manikandan, Palani,Karunakaran, Jayachandran,Varathan, Elumalai,Schreckenbach, Georg,Mohanakrishnan, Arasambattu K.
, p. 15317 - 15320 (2020)
Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes. This journal is
Ceria-promoted Co@NC catalyst for biofuel upgrade: synergy between ceria and cobalt species
Wang, Bowei,Gao, Ruixiao,Zhang, Dan,Zeng, Yuyao,Zhang, Fangying,Yan, Xilong,Li, Yang,Chen, Ligong
, p. 8541 - 8553 (2021)
Ceria-promoted Co@NC (NC, N doped carbon) catalysts are prepared by pyrolysis of biomass materials. Characterization results indicate that ceria and Co species facilitate the distribution of each other due to the formation of a Ce-O-Co solid solution. The specific surface area of the catalyst increased from 378.77 to 537.7 m2g?1viathe introduction of ceria. The electron transfer from Co to Ce further enhanced their interaction, and Co species facilitate the formation of more defective oxygen vacancies on ceria, which are beneficial to the activities of catalytic hydrogenation and catalytic transfer hydrogenation (CTH), respectively. Thus, Co/Ce@NC (0.99% Co loading) pyrolyzed at 850 °C exhibits excellent performance in the hydrodeoxygenation (HDO) of vanillin with high metal utilization. Catalytic hydrogenation and CTH coexisted in the presence of H2and ethanol, and >99% yield of creosol can be obtained in each of them. The reaction processes are monitored. No intermediate is found in aqueous media, while ethoxymethyl-4-methoxy-2-phenol is detected in ethanol. Moreover, Co/Ce@NC presents outstanding stability and general applicability. This work provides new insights into the construction of M@NC (M, metal) catalysts and the HDO process of biofuel upgrade.
Role of transalkylation reactions in the conversion of anisole over HZSM-5
Zhu, Xinli,Mallinson, Richard G.,Resasco, Daniel E.
, p. 172 - 181 (2010)
Conversion of anisole, a typical component of bio-oil, was studied over an HZSM-5 zeolite at varying space times (W/F), reaction temperatures, type of carrier gas, and concentration of water in the feed. Several bimolecular and unimolecular reactions are proposed to explain the evolution of products observed. The bimolecular reactions include the following transalkylation reactions: (a) anisoles to phenol and methylanisole; (b) phenol and methylanisole to cresols; (c) phenol and anisole to cresol and phenol; (d) methylanisole and cresol to phenol and xylenol. A pseudo first-order kinetic model based on these bimolecular reactions was found to describe well the observed product distribution as a function of W/F. It is observed that shape selectivity effects prevail over electrophilic substitution and thermodynamic equilibrium effects in the formation of methylanisole isomers. However, the opposite is true for the distribution of cresol isomers. The kinetic analysis indicates that the contribution of unimolecular reactions such as isomerization is much lower than that of bimolecular reactions. The carrier gas composition was found to have a moderate effect on catalyst activity. When H2 was used as a carrier, catalyst stability showed a moderate improvement in comparison to the runs under He. However, a remarkable increase in catalytic activity was observed upon the addition of water in the feed.
C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids
Mankad, Neal P.,Toste, F. Dean
, p. 12859 - 12861 (2010)
Previously, alkylgold(III) fluorides have been proposed as catalytic intermediates that undergo C-C coupling with reagents such as arylboronic acids in Au(I)/Au(III) cross-coupling reactions. Here is reported the first experimental evidence for this elementary mechanistic step. Complexes of the type (NHC)AuMe (NHC = N-heterocyclic carbene) were oxidized with XeF2 to yield cis-(NHC)AuMeF2 products, which were found to be in equilibrium with their fluoride-dissociated, dimeric [(NHC)AuMe(μ-F)] 2[F]2 forms. In one case, a monomeric cis-(NHC)AuMeF 2 complex was favored exclusively in solution, and it was found to react with a variety of ArB(OH)2 reagents to yield Ar-CH3 products.
Dual-pathway chain-end modification of RAFT polymers using visible light and metal-free conditions
Discekici, Emre H.,Shankel, Shelby L.,Anastasaki, Athina,Oschmann, Bernd,Lee, In-Hwan,Niu, Jia,McGrath, Alaina J.,Clark, Paul G.,Laitar, David S.,De Alaniz, Javier Read,Hawker, Craig J.,Lunn, David J.
, p. 1888 - 1891 (2017)
We report a metal-free strategy for the chain-end modification of RAFT polymers utilizing visible light. By turning the light source on or off, the reaction pathway in one pot can be switched between either complete desulfurization (hydrogen chain-end) or simple cleavage (thiol chain-end), respectively. The versatility of this process is exemplified by application to a wide range of polymer backbones under mild, quantitative conditions using commercial reagents.
SPONTANEOUS DEOXYGENATION OF THE PRODUCTS OF THE ADDITION OF MeYbI and PhYbI TO PARA-BENZOQUINONE
Syutkina, O. P.,Rybakova, L. F.,Petrov, E. S.,Beletskaya, I. P.
, p. 1955 - 1956 (1986)
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Fluorination and Fluorodemercuration of Aromatic Compounds with Acetyl Hypofluorite
Visser, Gerard W. M.,Bakker, Cees N. M.,Halteren, Bert W. v.,Herscheid, Jacobus D. M.,Brinkman, Gerard A.,Hoekstra, Arend
, p. 1886 - 1889 (1986)
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Internal Coordination at Tin Promotes Selective Alkyl Transfer in the Stille Coupling Reaction
Vedejs, Edwin,Haight, Anthony R.,Moss, William O.
, p. 6556 - 6558 (1992)
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Arylation of aliphatic alcohols with tri-p-tolylbismuth and tri-p-tolylbismuth diacetate in the presence of a copper salt
Dodonov, V. A.,Starostina, T. I.,Kuznetsova, Yu. L.,Gushchin, A. V.
, p. 151 - 153 (1995)
Tri-p-tolylbismuth diacetate in the presence of a catalytic amount of a copper(II) salt (1 : 0.02, mol/mol) and tri-p-tolylbismuth in the presence of copper diacetate (1 : 2) replace the hydrogen atom of the hydroxyl groups of methanol and butanol with a tolyl group at 80 deg C in up to 90percent yields. - Key words: tri-p-tolylbismuth, tri-p-tolylbismuth diacetate, arylation; copper diacetate; methanol, butanol; alkyl tolyl ethers.
Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong
, p. 513 - 523 (2021/01/12)
Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.
A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light
Qiu, Wenting,Shi, Shuai,Li, Ruining,Lin, Xianfeng,Rao, Liangming,Sun, Zhankui
supporting information, p. 1255 - 1258 (2021/05/05)
A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.
