76837-21-3Relevant academic research and scientific papers
Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**
Brauer, Jan,Quraishi, Elisabeth,Kammer, Lisa Marie,Opatz, Till
supporting information, p. 18168 - 18174 (2021/11/30)
A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.
Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina
Charvieux, Aubin,Giorgi, Javier B.,Duguet, Nicolas,Métay, Estelle
supporting information, p. 4210 - 4216 (2018/10/02)
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO2-Al2O3 was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.
Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives
Kikuchi, Satoshi,Yoshida, Shunsuke,Sugawara, Yuudai,Yamada, Wataru,Cheng, Hau-Man,Sekine, Kohei,Iwakura, Izumi,Ikeno, Taketo,Yamada, Tohru
scheme or table, p. 698 - 717 (2011/09/14)
A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was f
Synthesis of 1,1-organodiboronates via Rh(I)CI-catalyzed sequential regioselective hydroboration of 1-alkynes
Endo, Kohei,Hirokami, Munenao,Shibata, Takanori
scheme or table, p. 1331 - 1335 (2009/10/23)
A Rh(I)Cl-DPPB-complex-catalyzed sequential hydroboration of aryl alkynes and aliphatic alkynes was achieved. The reaction proceeded with almost perfect regioselectivity to afford 1,1-organodiboronate compounds in moderate to good yield. Georg Thieme Verl
4,5 Dihydro-(1H)-Pyrazole Derivatives as Cannabinoid CB1 Receptor Modulators
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Page/Page column 12, (2009/01/24)
The invention is directed to 4,5-dihydro-(1H)-pyrazole (pyrazoline) derivatives as cannabinoid CB1 receptor modulators, to pharmaceutical compositions comprising these compounds, to methods for their syntheses, to methods for preparing novel intermediates useful for their syntheses, and to methods for preparing compositions. The invention also relates to the uses of compounds and compositions administered to patients to achieve a therapeutic effect in multiple sclerosis, traumatic brain injury, pain including chronic pain, neuropathic pain, acute pain and inflammatory pain, osteoporosis, appetite disorders, epilepsy, Alzheimer's disease, Tourette's syndrome, cerebral ischaemia, emesis, nausea, and gastrointestinal disorders. Compounds of the present disclosure are directed to formula (I): wherein the substituents have the definitions given in the specification.
Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones
Sugawara, Yudai,Yamada, Wataru,Yoshida, Shunsuke,Ikeno, Taketo,Yamada, Tohru
, p. 12902 - 12903 (2008/03/27)
In the presence of a catalytic amount of a silver salt with DBU under a CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α,β-unsaturated carbonyl compounds in high yield. An iso
Branch-selective intermolecular hydroacylation: Hydrogen-mediated coupling of anhydrides to styrenes and activated olefins
Hong, Young-Taek,Barchuk, Andriy,Krische, Michael J.
, p. 6885 - 6888 (2007/10/03)
(Chemical Equation Presented) Branching out with hydrogen: Hydrogenation of symmetric or mixed carboxylic anhydrides in the presence of styrenes or activated olefins generates intermolecular hydroacylation products. The use of cationic rhodium catalysts ligated by triphenylarsine (Ph3As) results in the formation of branched coupling products as single regioisomers in high yields (see scheme; cod = cycloocta-1,5-diene, ArF = 3,5-(CF 3)2C6H3).
Oxidative Generation of 1-Nitroalkyl Radicals and Their Addition Reaction to Olefins
Arai, Noriyoshi,Narasaka, Koichi
, p. 2525 - 2534 (2007/10/03)
1-Nitroalkyl radicals are generated by oxidation of potassium salt of 1-aci-nitroalkanes with ammonium hexanitratocerate(IV). When the oxidation is carried out in the presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals onto the olefins proceeds to afford β-nitro ketones, which are further converted to α,β-unsaturated ketones in high yield. Stereoselective construction of fused ring systems is achieved by intramolecular addition of 1-nitroalkyl radicals.
Generation of α-Nitroalkyl Radicals by Oxidation of Nitronate Anions with Cerium(IV) Ammonium Nitrate and Their Addition Reaction to Electron-Rich Olefins
Arai, Noriyoshi,Narasaka, Koichi
, p. 987 - 988 (2007/10/03)
α-Nitroalkyl radicals are generated by oxidation of nitronate anions with cerium(IV) ammonium nitrate.When the reactions are carried out in hte presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals proceeds to afford β-nitroketones, which are further converted to α,β-unsaturated ketones in good yield.
The Oxidation of Akoxytributylstannanes with Copper(II) Bromide
Yamaguchi, Jun-ichi,Takeda, Takeshi
, p. 423 - 426 (2007/10/02)
The oxidation of alkoxytributylstannanes with copper(II) bromide in the presence of lithium bromide and t-butoxytributylstannane gave the corresponding carbonyl compounds in good yields under mild reaction conditions.
