118993-65-0Relevant academic research and scientific papers
Ligand-free Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH3CN with Sub-stoichiometric Amount of Mo(CO)6 as CO Source
Sun, Nan,Sun, Qingxia,Zhao, Wei,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 2117 - 2123 (2019/03/28)
A new method for the synthesis of diaryl and heterodiaryl ketones has been established based on the palladium-catalyzed carbonylative Suzuki coupling approach with sub-stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross-coupling reaction in aqueous CH3CN at 50 °C, affording the corresponding ketones in good to excellent yields. The newly developed method was easy to operate under mild conditions with high efficiency. (Figure presented.).
MeZnOMe-mediated reaction of aldehydes with Grignard reagents: A glance into nucleophilic addition/Oppenauer oxidation pathway
Fu, Ying,Ma, Xian-Zhen,Shi, Chun-Zhao,Shen, Tong,Du, Zhengyin
, (2018/07/31)
A novel organozincate of RMgX ?MeZnOMe ?LiCl type, formed in situ via transmetalation of Grignard reagent RMgBr ?LiCl with MeZnOMe, is shown to be an excellent organometallic species in the nucleophilic addition/Oppenauer oxidation of aldehydes to generate aromatic ketones in high yield. This transformation allows quick access to structurally diverse aryl, heteroaryl, benzyl and alkyl ketones with broad substrate scope and excellent functional group tolerance.
Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones
Jadhav, Sanjay,Rashinkar, Gajanan,Salunkhe, Rajashri,Kumbhar, Arjun
supporting information, p. 3201 - 3204 (2017/07/27)
A simple, efficient and metal-free route for the synthesis of dissymmetric ketones through Suzuki type cross-coupling reaction has been established. This strategy signifies an attractive, cost-effective and operationally convenient tool for the synthesis of a wide range of dissymmetric ketones. Although conventional routes for the synthesis of ketones have been widely used, the potential challenge with these methods is functional group tolerance. The reported metal-free method represents a reaction with moderate functional group tolerance. The procedure is operationally convenient and shows broad substrate scope with good to excellent product yields.
Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
, p. 12018 - 12032 (2015/01/16)
A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
Tandem nucleophilic addition-Oppenauer oxidation of aromatic aldehydes to aryl ketones with triorganoaluminium reagents
Fu, Ying,Yang, Yanshou,Hügel, Helmut M.,Du, Zhengyin,Wang, Kehu,Huang, Danfeng,Hu, Yulai
supporting information, p. 4429 - 4432 (2013/08/23)
In the presence of pinacolone, the in situ prepared triorganoaluminium reagents reacted with aromatic aldehydes to give ketones in moderate to high yield. We propose that the products are formed via a tandem organoaluminium reagents addition-Oppenauer oxidation sequence. The Royal Society of Chemistry 2013.
Efficient, recyclable and phosphine-free carbonylative Suzuki coupling reaction using immobilized palladium ion-containing ionic liquid: Synthesis of aryl ketones and heteroaryl ketones
Khedkar, Mayur V.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
, p. 7791 - 7797 (2013/06/27)
The carbonylative Suzuki coupling reaction of aryl and heteroaryl iodides was studied by using immobilized palladium ion-containing ionic liquid (ImmPd-IL). The protocol was optimized with respect to various reaction parameters, applied to a wide variety of substituted aryl/heteroaryl iodides and various aryl/heteroaryl boronic acids with different steric and electronic properties, and afforded the corresponding products in good to excellent yield. This is an efficient, heterogeneous catalyst which avoids the use of phosphine ligands, and its reusability was tested in up to four consecutive cycles. The recycled catalyst was characterized by using XPS analysis.
4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors
Hartman,Halczenko,Smith,Sugrue,Mallorga,Michelson,Randall,Schwam,Sondey
, p. 3822 - 3831 (2007/10/02)
A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potentia
4-(benzoyl)thiophene(or furan)-sulfonamide and derivatives thereof for the topical treatment of elevated intraocular pressures
-
, (2008/06/13)
4-(benzoyl)thiophene(or furan)-2-sulfonamide and derivatives thereof are useful for the topical treatment of elevated intraocular pressure.
