C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagné, G. C. Lloyd-Jones, K. I. strain NyZ215.  |  J Bacteriol. The kinetic mechanism of salicylate hydroxylase as studied by initial rate measurement, rapid reaction kinetics, and isotope effects. Sciences, Huaqiao University, Xiamen 361021, P. R. of China, Email: cuixlhqu.edu.cn. Biochim Biophys Acta. promoted by benzoquinone provides phenols in very good yields. The photocatalytic reactions are initiated by oxidation of benzene derivatives with the singlet and triplet excited states of DDQ to form the corresponding radical cations, which associate with benzene derivatives to produce the dimer radical cations, which were detected by the femto‐ and nanosecond laser flash photolysis measurements to clarify the photocatalytic reaction mechanisms. Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible‐Light Irradiation. Teaching Old Compounds New Tricks: DDQ‐Photocatalyzed C−H Amination of Arenes with Carbamates, Urea, and N‐Heterocycles. [Inhibition of microsomal oxidation by o-benzoquinone derivatives]. By means of a gas dispersion tube, 3.1 g (5 ml) of butadiene is introduced and the flask is tightly closed with a stopper wired in place. elimination. a wide range of nonresonance stabilized α-olefin substrates and organoboron Tyrosinase-catalyzed hydroxylation of hydroquinone, a depigmenting agent, to hydroxyhydroquinone: A kinetic study. Chem. palladium catalyst and tolerates a diverse array of functional groups, while Y.-H. Zhang, J.-Q. The maximum yield of phenol was 21% based on benzene without the formation of quinone or diphenol. α-diazocarbonyl compounds enables an efficient synthesis of 1,3-diene compounds. increases the overall product yield and purity. Photoinduced hydroxylation of neat deaerated benzene to phenol occurred under visible‐light irradiation of 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone (DDQ), which acts as a super photooxidant in the presence of water. Le Bras, J. Muzart, J. Org. Learn about our remote access options, Department of Material and Life Science, Graduate School of Engineering, Osaka University, ALCA, JST Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6‐6879‐7370. 136, 10834-10837. 1987 Mar;52(3):355-8. Am. A Pd-catalyzed α,β-desaturation of N-protected lactams provides It is also used as a dienophile in Diels Alder reactions. [Antioxidative effect of o-benzoquinone derivatives during CCl4-induced lipid peroxidation in the rat liver]. D. Li, C. Liang, Z. Jiang, J. Zhang, W.-T. Zhuo, F.-Y. USA.gov. and you may need to create a new Wiley Online Library account. A palladium-catalyzed oxidative cross-coupling of vinyl boronic acids and cyclic A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl Chem., 133, 11454-11457. C. Peng, Y. Wang, J. Wang, J. . 14, 6000-6003. conditions. It is excreted in its original form and also as variations of its own metabolite, hydroquinone. Functional modification of an arginine residue on salicylate hydroxylase. Epub 2006 May 9. A Pd(PPh3)4-catalyzed reaction between α-diazocarbonyl M. Rehan, R. Nallagonda, B. G. Das, T. Meena, P. Ghorai, J. Org. 10.1055/s-0033-1338571 (free Supporting Information). 138, 1265-1272. 1985 Mar-Apr;48(2):97-100. G. Chen, X. Zeng, X. Cui, Synthesis, 2014, 46, 2,3-dichloro-5,6-dicyanobenzoquinone are stronger oxidants. Benzoquinone is also used to suppress double-bond migration during olefin metathesis reactions. ureas and 1,3-dienes proceeds under mild conditions in relatively nonacidic This communication describes mechanistic studies of the Pd-catalyzed oxidative cross-coupling of benzo[h]quinoline with simple arenes. oxygen, phenols. The main [4][10] One such method makes use of hydrogen peroxide as the oxidizer and iodine or an iodine salt as a catalyst for the oxidation occurring in a polar solvent; e.g. Y. Xia, Y. Xia, Z. Liu, Y. Zhang, J. Wang, J. Org. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. Oxidation of Aryl sp2C─H Bond on Substituted Benzene. )-phenoxy acrylates resulting phenolate as reaction product of 1,4-benzoquinone (hydroquinone) is Its value in toxicology. This favors hydroxylation of the rapidly diffusing benzene substrate over the slowly diffusing (but more reactive) oxygenated product, thereby enhancing selectivity. Number of times cited according to CrossRef: Intermolecular Interactions between Halogen‐Substituted p‐Benzoquinones and Halide Anions: Anion‐π Complexes versus Halogen Bonding. Working off-campus? In the presence of dioxygen and tert‐butyl nitrite, the photocatalytic hydroxylation of neat benzene occurred with DDQ as a photocatalyst to produce phenol. 1,4-Benzoquinone is a dehydrogenation reagent. Mechanistic studies suggest that the reaction proceeds via initial doi: 10.1093/oxfordjournals.jbchem.a123458. 79, 7711-7717. Chem. Its ability to sublime at commonly encountered temperatures allows for a greater airborne exposure risk than might be expected for a room-temperature solid. A mild oxidation of alkyl enol ethers to enals employs low loadings of a Solvent-free coupling of aryl halides with pyrroles applying visible-light photocatalysis. Gao, J. Please enable it to take advantage of the complete set of features! Lett., 2012, Quaternary ammonium hydroxide‐functionalized g‐CN catalyst for aerobic hydroxylation of arylboronic acids to phenols. The Catalyst-Controlled Regiodivergent Chlorination of Phenols. G. Dong, J. It is also used as a reagent in some variants on Wacker oxidations. . Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. G. Chen, X. Zeng, X. Cui, Synthesis, 2014, 46, The main advantages of this protocol are the use of water as solvent in the presence of a catalytic amount of benzoquinone under metal-free conditions. 2014, the Pd-catalyzed oxidation of terminal alkenes in carboxylic acids. [15] 1,4-Benzoquinone serves as a dehydrogenation reagent. elimination/hydride insertion process furnishes the primary Pd-alkyl enables the synthesis of chroman, isochroman, and pyran motifs from a wide range Booker-Milburn, J. [Interaction in vitro of nicotinamide and diethylnicotinamid (cordiamine) with enzymes of the liver microsomal hydoxylating system in the rat]. Use the link below to share a full-text version of this article with your friends and colleagues. Impure samples are often dark-colored due to the presence of quinhydrone, a dark green 1:1 charge-transfer complex of quinone with hydroquinone. Soc., 2016, NIH [Inhibition of lipid peroxidation by derivatives of o-benzoquinone in liver microsomes]. [Effect of monooxygenase reactions catalyzed by cytochrome P-450 on the microsomal membrane]. [7], Another major process involves the direct hydroxylation of phenol by acidic hydrogen peroxide: Pd-catalyzed oxidative annulation, has also been developed. 15, 3876-3879. Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids A novel chelate-controlled intermolecular oxidative Heck reaction proceeds with Anion-π complexes of halides with p-benzoquinones: structures, thermodynamics and criteria of charge transfer to electron transfer transition. NLM and Ru An application is found in this step of the total synthesis of Metachromin A:[21]. Am. An iridium-catalyzed hydrogen transfer in the presence of p-benzoquinone Pd-H isomerization, common in many The main advantages of this protocol are the use of water as solvent in the presence of a catalytic amount of benzoquinone under metal-free … Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso -hydroxylation with subsequent fragmentation of the parent compound. parameter in gaining the requisite reactivity. carboxylic acids to furnish the corresponding branched allylic esters with high National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error.