5581-75-9Relevant academic research and scientific papers
Evidence for the involvement of silver nanoclusters during the wolff rearrangement of α-diazoketones
Sudrik, Surendra G.,Maddanimath, Trupti,Chaki, Nirmalya K.,Chavan, Sambhaji P.,Chavan, Subhash P.,Sonawane, Harikisan R.,Vijayamohanan
, p. 2355 - 2358 (2003)
(Matrix presented) In situ-generated silver nanoclusters(Agn) during the reduction of either silver(I) oxide or other salts presumably catalyze the Wolff rearrangement of α-diazoketones. Their optical, physical, and catalytic properties depend
Synthetic method of acid compound
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Paragraph 0028-0032; 0049, (2020/08/25)
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of an acid compound. An acid anhydride compound and an alkyl bromide or a functionalized alkyl bromide are subjected to a cross-electrophilic coupling reaction to synthesize an acid compound, so that the application of the alkyl bromide in the cross-electrophilic coupling reaction is expanded, and a novel non-traditional method for chemically and selectively constructing a carbon-carbon bond through a decarburization process is provided. The synthesis method is simple, economic, green and environment-friendly, and has wider applicability or is suitable for large-scale production.
Site-Selective, Remote sp3 C?H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis
Sahoo, Basudev,Bellotti, Peter,Juliá-Hernández, Francisco,Meng, Qing-Yuan,Crespi, Stefano,K?nig, Burkhard,Martin, Ruben
supporting information, p. 9001 - 9005 (2019/06/24)
A photoinduced carboxylation of alkyl halides with CO2 at remote sp3 C?H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.
Synthesis of Elongated Esters from Alkenes
Miura, Tomoya,Funakoshi, Yuuta,Nakahashi, Junki,Moriyama, Daisuke,Murakami, Masahiro
supporting information, p. 15455 - 15459 (2018/10/31)
A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible-light irradiation of an ester-stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester.
CARBOXAMIDE INHIBITORS
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Paragraph 0395-0397, (2017/08/01)
The present invention provides a compound of formula I The compounds of formula I demonstrate properties as Smurf-1 inhibitors and are thus useful in the treatment of a range of disorders, particularly pulmonary arterial hypertension.
Synthetic Applications and Mechanistic Studies of the Hydroxide-Mediated Cleavage of Carbon-Carbon Bonds in Ketones
Mazziotta, Andrea,Makarov, Ilya S.,Fristrup, Peter,Madsen, Robert
, p. 5890 - 5897 (2017/06/07)
The hydroxide-mediated cleavage of ketones into alkanes and carboxylic acids has been reinvestigated and the substrate scope extended to benzyl carbonyl compounds. The transformation is performed with a 0.05 M ketone solution in refluxing xylene in the presence of 10 equiv of potassium hydroxide. The reaction constitutes a straightforward protocol for the synthesis of certain phenyl-substituted carboxylic acids from 2-phenylcycloalkanones. The mechanism was investigated by kinetic experiments which indicated a first order reaction in hydroxide and a full negative charge in the rate-determining step. The studies were complemented by a theoretical investigation where two possible pathways were characterized by DFT/M06-2X. The calculations showed that the scission takes place by nucleophilic attack of hydroxide on the ketone followed by fragmentation of the resulting oxyanion into the carboxylic acid and a benzyl anion.
Palladium on carbon-catalyzed aqueous transformation of primary alcohols to carboxylic acids based on dehydrogenation under mildly reduced pressure
Sawama, Yoshinari,Morita, Kosuke,Asai, Shota,Kozawa, Masami,Tadokoro, Shinsuke,Nakajima, Junichi,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 1205 - 1210 (2015/04/22)
The catalytic dehydrogenation of alcohols to carbonyl products is a green sustainable oxidation with no production of waste except for hydrogen, which can be an energy source. Additionally, a reusable heterogeneous catalyst is valuable from the viewpoint of process chemistry and water is a green solvent. We have accomplished the palladium on carbon (Pd/C)-catalyzed dehydrogenation of primary alcohols to carboxylic acids in water under a mildly reduced pressure (800 hPa). The reduced pressure can be easily controlled by the vacuum controller of the rotary evaporator to remove the excess of generated hydrogen, which causes the reduction (reverse reaction) of aldehydes to alcohols (starting materials) and other undesirable side reactions. The present method is applicable to the reaction of various aliphatic and benzylic alcohols to the corresponding carboxylic acids, and the Pd/C could be reused at least 5 times.
Ketyl-type radicals from cyclic and acyclic esters are stabilized by SmI2(H2O)n: the role of SmI2(H 2O)n in post-electron transfer steps
Szostak, Michal,Spain, Malcolm,Procter, David J.
supporting information, p. 8459 - 8466 (2014/06/24)
Mechanistic details pertaining to the SmI2-H2O- mediated reduction and reductive coupling of 6-membered lactones, the first class of simple unactivated carboxylic acid derivatives that had long been thought to lie outside the reducing range of SmI2, have been elucidated. Our results provide new experimental evidence that water enables the productive electron transfer from Sm(II) by stabilization of the radical anion intermediate rather than by solely promoting the first electron transfer as originally proposed. Notably, these studies suggest that all reactions involving the generation of ketyl-type radicals with SmI2 occur under a unified mechanism based on the thermodynamic control of the second electron transfer step, thus providing a blueprint for the development of a broad range of novel chemoselective transformations via open-shell electron pathways.
Rhodium-on-carbon catalyzed hydrogen scavenger- and oxidant-free dehydrogenation of alcohols in aqueous media
Sawama, Yoshinari,Morita, Kosuke,Yamada, Tsuyoshi,Nagata, Saori,Yabe, Yuki,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 3439 - 3443 (2014/07/08)
The efficient and catalytic dehydrogenation of alcohols is a clean approach for preparing carbonyl compounds accompanied only by the generation of hydrogen gas. We have accomplished the heterogeneous rhodium-on-carbon catalyzed dehydrogenation of secondary, as well as primary, alcohols to the corresponding ketones and carboxylic acids in water under basic conditions. This journal is the Partner Organisations 2014.
Indium-mediated chemoselective deprotection and demonochlorination of 2,2,2-trichloroethyl esters
Mineno, Tomoko,Kansui, Hisao,Kunieda, Takehisa
, p. 5027 - 5030 (2008/02/10)
On treatment with indium metal, the 2,2,2-trichloroethyl carboxylates smoothly undergo deprotection to carboxylic acids and reductive demonochlorination to 2,2-dichloroethyl esters, sharply depending on their structures.
