33720-29-5Relevant academic research and scientific papers
Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation
Shen, Duyi,Wang, Hongyan,Zheng, Yanan,Zhu, Xinjing,Gong, Peiwei,Wang, Bin,You, Jinmao,Zhao, Yulei,Chao, Mianran
, p. 5354 - 5361 (2021/05/05)
A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.
Palladium-Catalyzed Synthesis of 1,2-Diketones from Aryl Halides and Organoaluminum Reagents Using tert-Butyl Isocyanide as the CO Source
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 636 - 641 (2020/01/31)
In this work, an interesting and practical procedure for the synthesis of 1,2-diketones from aryl halides and organoaluminum reagents has been developed. Employing tert-butyl isocyanide as the CO source and palladium as the catalyst, the desired 1,2-diketones were isolated in good to excellent yields with good functional group tolerance. Concerning the reaction partners, besides aryl halides, both alkyl- A nd arylaluminum reagents were all suitable substrates here.
Synthetic method of 1,2-diketone compound
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Paragraph 0051-0054, (2018/06/14)
The invention discloses a synthetic method of a 1,2-diketone compound. The method comprises the following steps: under room temperature, an alkyne compound is taken as a raw material, a Ru/C is takenas a catalyst, an oxidizing agent and sulfuric acid are added, acetonitrile and water with a volume ratio being 1-5:1 are taken as solvents, the materials are completely reacted at the temperature of20-30 DEG C, and a reaction solution is subjected to separating and purifying to obtain the 1,2-diketone compound. The method has the advantages that operation is simple, reaction time is short, yield(achieving to 100%) is high, substrate universality is wide, water and acetonitrile are taken as the primary solvents (the solvent acetonitrile is easily recovered and used), and a heterogeneous phase catalyst Ru/C is easily recovered. The synthetic method of the 1,2-diketone compound accords with green chemistry characteristic, and is very suitable for industrialization.
Synthesis of a new class of cationic Pd(II) complexes with 1,2,3-triazol-5-ylidene ligand and their catalytic application in the conversion of internal alkynes to 1,2-diketones
Shaik, Jeelani Basha,Ramkumar, Venkatachalam,Sankararaman, Sethuraman
supporting information, p. 1 - 8 (2018/02/19)
A new class of cationic Pd(II) complexes of the type [Pd(Tz)(Cl)(bipy)]+Cl? and [Pd (Tz)(Cl)(phen)]+Cl? (Tz = 1,4-diaryl-3-methyl-1,2,3-triazol-5-ylidene, bipy = 2,2′-bipyridine and phen = 1,10-phenanthroline) with various wing tip groups were synthesized from the corresponding 1,2,3-triazolium iodide via the corresponding chloro bridged dinuclear complexes [(Tz)(Cl)Pd(μ-Cl)2Pd(Cl)(Tz)]. The synthesized cationic complexes were screened for their catalytic activity of hydration of alkynes and found to be excellent towards the selective conversion of internal alkynes to the corresponding 1,2-diketones in good yields. A plausible mechanism was proposed for this conversion.
A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes
Chen, Hongyi,Zhang, Liming
, p. 11775 - 11779 (2015/10/05)
Donor-substituted acyl gold carbenes are challenging to access selectively by gold-promoted intermolecular oxidation of internal alkynes as the opposite regioisomers frequently predominate. By using alkynyl sulfones or sulfonates as substrates, the oxidative gold catalysis in the presence of substituted pyridine N-oxides offers regiospecific access to acyl/aryl, acyl/alkenyl, and acyl/alkoxy gold carbenes by in situ expulsion of sulfur dioxide. The intermediacies of these reactive species are established by their reactivities, including undergoing further oxidation by the same oxidant, cyclopropanation of styrenes, engaging in a [3+2] cycloaddition with α-methylstyrene, and conversion into dienones. Accept it: A desulfonylative approach was developed to regiospecifically access these underexplored acyl gold carbenes from either alkynyl aryl/alkenyl sulfones or alkynyl sulfonate substrates. The reactivities of these donor- and acceptor-substituted carbenes are examined.
Nitroaldol (Henry) reaction of 2-oxoaldehydes with nitroalkanes as a strategic step for a useful, one-pot synthesis of 1,2-diketones
Palmieri, Alessandro,Gabrielli, Serena,Sampaolesi, Susanna,Ballini, Roberto
, p. 36652 - 36655 (2015/05/05)
The nitroaldol (Henry) reaction of 2-oxoaldehydes with a variety of nitroalkanes, under basic heterogeneous conditions and microwave irradiation, affords 1,2-diketones in a one-pot way. The key step of the process involves the nitrous acid elimination fro
A highly efficient catalyst for selective oxidative scission of olefins to aldehydes: Abnormal-NHC-Ru(II) complex in oxidation chemistry
Daw, Prosenjit,Petakamsetty, Ramu,Sarbajna, Abir,Laha, Siladitya,Ramapanicker, Ramesh,Bera, Jitendra K.
supporting information, p. 13987 - 13990 (2015/01/08)
The utility and selectivity of the catalyst [Ru(COD)(L1)Br2] (1) bearing a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based abnormal N-heterocyclic carbene ligand L1 is demonstrated toward selective oxidation of C=C bonds to aldehydes and C=C bonds to α-diketones in an EtOAc/CH3CN/H2O solvent mixture at room temperature using a wide range of substrates, including highly functionalized sugar- and amino acid-derived compounds.
Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines
Igarashi, Tomohito,Tayama, Eiji,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information, p. 6874 - 6877 (2019/04/10)
A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.
Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles
Cui, Dong-Mei,Zhuang, Dan-Wen,Chen, Ying,Zhang, Chen
experimental part, p. 860 - 865 (2011/08/05)
A gold-catalyzed oxidation of arylallenes to form α-diketones and aldehydes in good yields is presented. Further directed synthesis of quinoxalines and benzimidazoles, via the condensation of the resulting α-diketones and aldehydes with benzene-1,2-diamine, was achieved in high yields.
Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones
Wang, Azhong,Jiang, Huanfeng,Li, Xianwei
supporting information; experimental part, p. 6958 - 6961 (2011/10/02)
A palladium-catalyzed carbonation-diketonization reaction of terminal alkenes via carbon-nitrogen bond cleavage under an atmosphere of oxygen has been developed. A series of 1,2-diketones were readily prepared from the reaction of aromatic terminal alkenes with nitroalkanes.
