66252-27-5Relevant academic research and scientific papers
A selective and cost-effective method for the reductive deuteration of activated alkenes
Li, Hengzhao,Zhang, Bin,Dong, Yanhong,Liu, Ting,Zhang, Yuntong,Nie, Haiyu,Yang, Ruoyan,Ma, Xiaodong,Ling, Yun,An, Jie
, p. 2757 - 2760 (2017)
A new single electron transfer reaction for the reductive deuteration of activated alkenes has been developed for the selective synthesis of α,β-dideuterio compounds. A cheap, stable and commercially-available sodium dispersion with high specific surface
Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals
Ou, Wei,Xiang, Xudong,Zou, Ru,Xu, Qing,Loh, Kian Ping,Su, Chenliang
supporting information, p. 6357 - 6361 (2021/02/16)
Site-specific incorporation of deuterium into drug molecules to study and improve their biological properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon–oxygen bonds
Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions
Li, Jiaming,Li, Jian,Ji, Xiaoliang,He, Runfa,Liu, Yang,Chen, Zebin,Huang, Yubing,Liu, Qiang,Li, Yibiao
, p. 7412 - 7417 (2021/10/01)
Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.
Electrochemical Hydrogenation with Gaseous Ammonia
Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
supporting information, p. 1759 - 1763 (2019/01/16)
As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
Method for constructing carbon-hydrogen bond by catalyzing alcohol dehydroxylation with palladium/platinum
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Paragraph 0114-0116; 0118, (2019/12/25)
The invention discloses a method for constructing a carbon-hydrogen (deuterium) bond. The method comprises the following step: in the presence of a palladium/platinum catalyst and aryl halide, an alcohol hydroxyl group of an alcohol and hydrogen (deuterium) gas is replaced by hydrogen (deuterium) to construct the carbon-hydrogen (deuterium) bond. According to the method, the palladium/platinum catalyst is used as a catalyst, the green hydrogen (deuterium) gas is used as a hydrogen (deuterium) source, efficient alcohol dehydroxylation is performed at room temperature to construct the carbon-hydrogen (deuterium) bond, and the method is particularly suitable for constructing the carbon-deuterium bond and can be widely applied to synthesis of deuterated drugs.
New photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds
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Paragraph 0063-0065; 0068, (2019/01/21)
The invention relates to a new photocatalytic fixed-point deuteration method for carbon-carbon unsaturated bonds. The method is characterized in that an olefin or alkyne compound and a deuterium source undergoes a deuteration reaction under the catalysis of a light source and a photocatalyst to obtain a deuterated product, wherein the deuterium source is deuterated water, deuterated alcohol or deuterated acid, and the reaction temperature is between room temperature and 80 DEG C. The fixed-point deuteration reaction of the olefin or alkyne compound is realized under the photocatalysis action of the photocatalyst with environmentally-friendly and cheap deuterated water or a deuteration reagent as a deuterium source to substitute deuterium gas. Compared with traditional deuteration reactions, the method has a higher selectivity, milder reaction conditions and higher economical suitability, and is suitable for large-scale deuterated chemical substance production.
Secondary amides as hydrogen atom transfer promoters for reactions of samarium diiodide
Chciuk, Tesia V.,Li, Anna M.,Vazquez-Lopez, Andres,Anderson, William R.,Flowers, Robert A.
supporting information, p. 290 - 293 (2017/11/27)
Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI2 in THF to estimate the extent of N-H bond weakening upon coordination. Mechanistic and synthetic studies demonstrate significant bond-weakening, providing a reagent system capable of reducing a range of substrates through formal hydrogen atom transfer.
A convenient method for palladium-catalyzed reductive deuteration of organic substrates using deuterated hypophosphite in D2O
Oba, Makoto
, p. 215 - 219 (2015/05/20)
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
Determination of the effective redox potentials of SmI2, SmBr2, SmCl2, and their complexes with water by reduction of aromatic hydrocarbons. Reduction of anthracene and stilbene by samarium(II) iodide-water complex
Szostak, Michal,Spain, Malcolm,Procter, David J.
, p. 2522 - 2537 (2014/04/17)
Samarium(II) iodide-water complexes are ideally suited to mediate challenging electron transfer reactions, yet the effective redox potential of these powerful reductants has not been determined. Herein, we report an examination of the reactivity of SmI2(H2O)n with a series of unsaturated hydrocarbons and alkyl halides with reduction potentials ranging from -1.6 to -3.4 V vs SCE. We found that SmI 2(H2O)n reacts with substrates that have reduction potentials more positive than -2.21 V vs SCE, which is much higher than the thermodynamic redox potential of SmI2(H2O) n determined by electrochemical methods (up to -1.3 V vs SCE). Determination of the effective redox potential demonstrates that coordination of water to SmI2 increases the effective reducing power of Sm(II) by more than 0.4 V. We demonstrate that complexes of SmI2(H 2O)n arising from the addition of large amounts of H 2O (500 equiv) are much less reactive toward reduction of aromatic hydrocarbons than complexes of SmI2(H2O)n prepared using 50 equiv of H2O. We also report that SmI 2(H2O)n cleanly mediates Birch reductions of substrates bearing at least two aromatic rings in excellent yields, at room temperature, under very mild reaction conditions, and with selectivity that is not attainable by other single electron transfer reductants.
The isolation of [Pd{OC(O)H}(H)(NHC)(PR3)] (NHC = N-heterocyclic carbene) and its role in alkene and alkyne reductions using formic acid
Broggi, Julie,Jurcik, Vaclav,Songis, Olivier,Poater, Albert,Cavallo, Luigi,Slawin, Alexandra M. Z.,Cazin, Catherine S. J.
supporting information, p. 4588 - 4591 (2013/05/09)
The [Pd(SIPr)(PCy3)] complex efficiently promotes a tandem process involving dehydrogenation of formic acid and hydrogenation of C-C multiple bonds using H2 formed in situ. The isolation of a key catalytic hydridoformatopalladium species, [Pd{OC(O)H}(H)(IPr)(PCy 3)], is reported. The complex plays a key role in the Pd(0)-mediated formation of hydrogen from formic acid. Mechanistic and computational studies delineate the operational role of the palladium complex in this efficient tandem sequence.
