- Abstraction of deuterium from dideuteroglycine by aryl radical: A model for 1,4-benzene diradical reactions with proteins
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Aryl radicals are generated by oxidation of aryl hydrazine with PbO2 or via photolysis of aryl iodide. Abstraction of deuterium from dideuteroglycine derivatives is demonstrated as a model for the possible reaction of 1,4-aryl diradicals with a
- Braslau, Rebecca,Anderson, Marc O.
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Read Online
- Method for synthesizing deuterated compound in aqueous phase solvent
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The invention belongs to the technical field of isotope labeling chemical synthesis, and discloses a method for synthesizing a deuterated compound in an aqueous phase solvent. The method is based on the following chemical reaction equation: a halide, diaz
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Paragraph 0092-0097
(2021/05/12)
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- Photoinduced catalyst-free deborylation-deuteration of arylboronic acids with D2O
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Herein, novel photoinduced catalyst-free deborylation-deuteration of arylboronic acids with D2O is reported. The protocol was compatible with a variety of functionalities, including halogen, alkoxy, cyano, sulfonyl, trimethylsilyl, trifluoromethoxy, alkyl, hydroxyl, free acid, amide, and heteroaromatic rings. A wide range of deuterated products were obtained in good yields with a high level of deuteration. This method provides a green and practical pathway to synthesize deuterium labelled compounds under mild conditions.
- Lang, Yatao,Li, Chao-Jun,Peng, Xiangjun,Zeng, Huiying
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supporting information
p. 6323 - 6327
(2020/11/09)
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- Water Compatible Hypophosphites- d2 Reagents: Deuteration Reaction via Deutero-deiodination in Aqueous Solution
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Contrary to conventional deuteration approaches which typically entail deuterated solvents and/or moisture exclusion, an unprecedented deutero-deiodination reaction attainable in aqueous (H2O) solution is presented herein. By utilizing the stability of inorganic deuterated calcium/sodium hypophosphites against wayward H/D isotopic exchange within pH 2.5-11.7, these shelf-stable, nontoxic, cost-effective, and environmentally benign deuteration reagents mediate deuteration of a broad range alkyl and aryl iodides with ample isotopic incorporation in aqueous (H2O) solution.
- Fang, Jing,Li, Ting,Meng, Lingkui,Song, Zejin,Wan, Qian,Zeng, Jing,Zhao, Xiang
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supporting information
(2020/03/13)
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- Continuous-flow catalytic deuterodehalogenation carried out in propylene carbonate
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A selective continuous-flow (CF) deuterodehalogenation approach is described performed in propylene carbonate, which is considered as one of the greenest solvents. Various CF technologies are known for hydrodehalogenation reactions; however, they are not
- Orsy, Gy?rgy,Fül?p, Ferenc,Mándity, István M.
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supporting information
p. 956 - 961
(2019/03/11)
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- A preparing method of deuterated aromatic compounds
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The invention belongs to the field of chemical synthesis, particularly a preparing method of deuterated aromatic compounds. The method includes subjecting an aryl halide, as an initial raw material, to a palladium catalyzed carbon-halogen bond reduction r
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Paragraph 0032; 0033
(2019/01/08)
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- A convenient method for palladium-catalyzed reductive deuteration of organic substrates using deuterated hypophosphite in D2O
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A convenient method for the deuteration of organic substrates using deuterated hypophosphite as the deuterium source was investigated. Transfer deuteration of organic substrates, such as aromatic halides, alkenes, alkynes, epoxides, and O-benzyl derivativ
- Oba, Makoto
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p. 215 - 219
(2015/05/20)
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- Two-chamber hydrogen generation and application: Access to pressurized deuterium gas
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Hydrogen and deuterium gas were produced and directly applied in a two-chamber system. These gaseous reagents were generated by the simple reaction of metallic zinc with HCl in water for H2 and DCl in deuterated water for D2. The setup proved efficient in classical Pd-catalyzed reductions of ketones, alkynes, alkenes, etc. in near-quantitative yields. The method was extended to the synthesis and isotope labeling of quinoline and 1,2,3,4-tetrahydroquinoline derivatives. Finally, CX-546 and Olaparib underwent efficient Ir-catalyzed hydrogen isotope exchange reactions.
- Modvig, Amalie,Andersen, Thomas L.,Taaning, Rolf H.,Lindhardt, Anders T.,Skrydstrup, Troels
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p. 5861 - 5868
(2014/07/08)
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- CAN-mediated oxidation of electron-deficient aryl and heteroaryl hydrazines and hydrazides
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Aryl and heteroaryl hydrazines and hydrazides were successfully oxidised using CAN, deriving dehydrazinated products. The reaction pathway strongly depends on the nature of the substrate, resulting in the formation of hydrocarbons or alkoxy derivatives. When deuterated solvents such as methanol-d4 or acetonitrile-d3 were used, a regiospecific incorporation of deuterium was achieved. Georg Thieme Verlag Stuttgart.
- ?tefane, Bogdan,Polanc, Slovenko
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scheme or table
p. 1279 - 1282
(2009/04/06)
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- Facile and convenient method of deuterium gas generation using a Pd/C-catalyzed H2-D2 exchange reaction and itsapplication to synthesis of deuterium-labeled compounds
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The Pd/C-catalyzed H2-D2 exchange reaction using a H2-D2O combination provided a general, efficient and environmentally friendly route for the preparation of deuterium gas (D 2). H2 sealed
- Kurita, Takanori,Aoki, Fumiyo,Mizumoto, Takuto,Maejima, Toshihide,Esaki, Hiroyoshi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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experimental part
p. 3371 - 3379
(2009/04/10)
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- Complete replacement of H2 by D2 via Pd/C-catalyzed H/D exchange reaction
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(Chemical Equation Presented) A general and in situ D2 gas generation method using 10% Pd/C-catalyzed H2-D2 exchange reaction in a H2-D2O system has been developed. H 2 gas sealed in a reac
- Sajiki, Hironao,Kurita, Takanori,Esaki, Hiroyoshi,Aoki, Fumiyo,Maegawa, Tomohiro,Hirota, Kosaku
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p. 3521 - 3523
(2007/10/03)
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- Radical reaction by a combination of phosphinic acid and a base in aqueous media
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Treatment of various organic halides with phosphinic acid (hypophosphorous acid) in aqueous ethanol in the presence of a radical initiator and a base gave the corresponding reduced products in high yields. Addition of a base is indispensable for the reduction of halides by phosphinic acid. Allylic ether of o-iodophenol or 2-haloalkanal allylic acetal underwent radical cyclization under the same conditions to afford the corresponding cyclic product in excellent yield. Deuterated phosphinic acid was found to be an efficient chain carrier for the radical deuteration of organic halides. For example, a deuterium oxide solution of deuterated phosphinic acid, potassium carbonate, 2,2′-azobis(isobutyramidine) dihydrochloride as an initiator, and p-iodobenzoic acid was heated at reflux to give p-deuteriobenzoic acid in 94% yield. A mixed dioxane/D2O solvent system combined with DBU and potassium peroxodisulfate was crucial to deuterate hydrophobic substrates in high yields and with high deuterium incorporation. Complete deuterium incorporation was accomplished only by the reaction in D2O without an organic cosolvent and an organic base.
- Yorimitsu,Shinokubo,Oshima
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p. 225 - 235
(2007/10/03)
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- Regiospecific fragmentation of benzene derivatives: Synthetic and analytical applications
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The cycloadducts formed from arenes and tetrachloro- and tetrafluorobenzyne have been shown to undergo specific addition-fragmentation reactions. These sequences are both simple syntheses of arenes with unusual substitution patterns and a convenient alternative to the other methods currently available for assaying the isotopic distribution in [14C]-labelled benzene derivatives.
- Hales, Neil J.,Heaney, Harry,Hollinshead, John H.,Ley, Steven V.
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p. 7755 - 7776
(2007/10/02)
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- Cross-conjugated compounds: microwave spectrum and ring planarity of 3-methylene-1,4-cyclohexadiene
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The unstable 3-methylene-1,4-cyclohexadiene, an isomer of toluene, has been prepared from benzoic acid.The hydrocarbon can be handled quite easily in the solid state, and in the gas phase at low pressures.Rotational transitions have been measured from 12
- Hutter, Wolfgang,Bodenseh, Hans-Karl,Koch, Andreas
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- PREPARATION OF DEUTERIATED 1-PHENYLETHANOLS BY REDUCTIVE DEHALOGENATION OF THE CORRESPONDING HALOGENOACETOPHENONES WITH RANEY ALLOYS IN AN ALKALINE DEUTERIUM OXIDE SOLUTION
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Deuteriated 1-phenylethanols were prepared by reductive dehalogenation of the corresponding halogenoacetophenones with Raney Ni-Al and Cu-Al alloys in 5percent NaOD-D2O solution.It was found that the Ni-Al alloy introduced greater than expected numbers of deuterium atoms in the phenyl ring, but the expected deuteriated 1-phenylethanols were obtained in high yield and in high isotopic purity when Raney Cu-Al alloy was used.
- Tashiro, Masashi,Mataka, Shuntaro,Nakamura, Hiroshi,Nakayama, Kouji
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p. 179 - 182
(2007/10/02)
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- Preparation of All the Possible Ring-deuteriated Benzoic Acids by Reductive Dehalogenation of the Corresponding Halogenobenzoic Acids with Raney Alloys in an Alkaline Deuterium Oxide Solution
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All the possible undeuteriated benzoic acids were prepared mainly by treatment of the corresponding bromobenzoic acid with Raney Cu-Al alloy in 10percent NaOD-D2O solution. 5>Benzoic acid was obtained from pentafluorobenzoic acid by a similar reaction.However, only 4>benzoic acid was prepared by decarboxylation of 4>phthalic acid.
- Tashiro, Masashi,Nakayama, Kouji,Fukata, Gouki
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p. 2315 - 2318
(2007/10/02)
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- REDUCTION OF HALOBENZOIC ACIDS TO DEUTERATED BENZOIC ACIDS WITH RANEY ALLOYS IN NaOD-D2O SOLUTION
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Reduction of bromobenzoic acids with Raney Cu-Al alloy in 10percent NaOD-D2O solution afforded the corresponding deuterated benzoic acids in high yields and in high isotopic purities.However, use of Raney Ni-Al alloy instead of Cu-Al alloy leads to the in
- Tashiro, Masashi,Nakayama, Kouji,Fukata, Gouki
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p. 359 - 362
(2007/10/02)
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