62507-47-5Relevant academic research and scientific papers
Recyclable polyetheretherketone fiber-supported N-heterocyclic carbene catalysts for nucleophilic acylation of fluorobenzenes
Shi, Xian-Lei,Sun, Benyu,Hu, Qianqian,Liu, Kun,Li, Pengyu,Wang, Juanjuan
supporting information, p. 11390 - 11393 (2020/10/12)
We report for the first time a novel support of polyetheretherketone fiber for the synthesis of recyclable N-heterocyclic carbene (NHC) catalysts. The fiber catalysts were verified in nucleophilic acylation of fluorobenzenes with superior catalytic activities, and successfully recycled by a tiny pair of tweezers over 21 cycles with minimal loss of performance.
Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones
Higashi, Shoko,Uno, Sota,Ohsuga, Yui,Noumi, Maiko,Saito, Ryota
supporting information, (2020/10/12)
Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the presence of Pd(PPh3)4 and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically suppressed by simply adding Et3SiH to the reaction mixture, which reduces the amount of biaryl impurities in the products.
Total Synthesis of Termicalcicolanone A via Organocatalysis and Regioselective Claisen Rearrangement
Ito, Saki,Kitamura, Taiki,Arulmozhiraja, Sundaram,Manabe, Kei,Tokiwa, Hiroaki,Suzuki, Yumiko
supporting information, p. 2777 - 2781 (2019/04/30)
A total synthesis of an anticancer xanthone natural product termicalcicolanone A utilizing multiple nucleophilic aromatic substitutions and pericyclic reactions has been developed. The pyrano[3,2-b]xanthen-6-one scaffold was constructed via NHC-catalyzed
Diarylketone preparation method
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Paragraph 0019, (2017/09/05)
The invention discloses a diarylketone preparation method. According to the method, substituted nitrobenzene and aromatic acetic ester are dissolved in an organic solvent, alkali is added, the mixture is subjected to a reaction in the air or oxygen atmosphere at the temperature of 10-60 DEG C for 0.5-24 h, and diarylketone is obtained; the mole ratio of substituted nitrobenzene to aromatic acetic ester is (0.5:1)-(5:1), and the mole ratio of alkali to aromatic acetic ester is (1:1)-(5:1). The method overcomes defects caused by the adoption of strong acid or expensive metal reagents or strong oxidizers and the like in the prior art and has the advantages as follows: 1) with air as an oxidizer, use of strong or expensive chemical oxidizers is avoided; 2) no transition metal catalysts are used, so that the condition that heavy metal ions are left in a product is avoided; 3) without inductive groups, surplus steps of introduction of the inductive groups and removal of the inductive groups are avoided; 4) acylation of ortho positions or para positions of nitro-aromatic compounds is directly realized, which cannot be realized with a classic Friedel-Crafts acylation method. The synthesis method plays an important role in preparing diarylketone, particularly industrial production of acylation products of ortho positions or para positions of the nitro-aromatic compounds.
Aerobic oxidative acylation of nitroarenes with arylacetic esters under mild conditions: Facile access to diarylketones
Li, Jiang-Sheng,Yang, Qian,Yang, Fan,Chen, Guo-Qin,Li, Zhi-Wei,Kuang, Yin-Jie,Zhang, Wei-Jing,Huang, Peng-Mian
, p. 140 - 145 (2017/12/27)
A facile and regioselective base-mediated aerobic oxidative acylation of nitroarenes to access diarylketones under mild conditions has been developed. It features the use of bench-stable and readily available arylacetates as acyl surrogates, and the absence of transition-metals and synthetic oxidants. This protocol involves a cascade CDC/oxidative decarboxylation process.
In situ generation of palladium nanoparticles: Ligand-free palladium catalyzed pivalic acid assisted carbonylative Suzuki reactions at ambient conditions
Zhou, Qing,Wei, Shaohua,Han, Wei
, p. 1454 - 1460 (2014/03/21)
Highly selective carbonylative Suzuki reactions of aryl iodides with arylboronic acids using an in situ generated nanopalladium system furnished products in high yields. The reactions were performed under ambient conditions and in the absence of an added ligand. The key to success is the addition of pivalic acid, which can effectively suppress undesired Suzuki coupling. The synthesis can be easily scaled up, and the catalytic system can be reused up to nine times. The nature of the active catalytic species are discussed.
Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
Luong, Martín,Domini, Claudia E.,Silbestri, Gustavo F.,Chopa, Alicia B.
, p. 43 - 48 (2013/02/21)
A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
N-heterocyclic carbene-catalyzed nucleophilic aroylation of fluorobenzenes
Suzuki, Yumiko,Ota, Shinya,Fukuta, Yoshinori,Ueda, Yuki,Sato, Masayuki
, p. 2420 - 2423 (2008/09/19)
(Chemical Equation Presented) In N-heterocyclic carbene (NHCs) catalyzed nucleophilic substitution of fluorobenzenes, fluoro groups are replaced by aroyl groups, which are derived from aromatic aldehydes. 1,3,4,5-Tetramethylimidazol- 2-ylidene is found to be an efficient catalyst. The catalyst loading can be reduced to 1 mol % without a significant decrease in the product yields. Polysubstituted benzophenones are synthesized from fluorobenzenes and benzaldehydes by the NHC-catalyzed aroylation.
Synthesis of Diaryl Ketones Catalyzed by Al2O 3-ZrO2/S2O82- Solid Superacid
Jin, Tong-Shou,Yang, Mi-Na,Feng, Guo-Liang,Li, Tong-Shuang
, p. 479 - 485 (2007/10/03)
The acylation of a variety of aromatic compounds with benzoyl chloride or its derivatives and catalytic amounts of Al2O3-ZrO 2/S2O82- solid superacid affords the corresponding diaryl ketones in good to excellent yields 75-93% at appropriate temperature.
4-Substituted anilides as selective melatonin MT2 receptor agonists
Epperson, James R.,Deskus, Jeffrey A.,Gentile, Anthony J.,Iben, Lawrence G.,Ryan, Elaine,Sarbin, Nathan S.
, p. 1023 - 1026 (2007/10/03)
A series of 4-substituted anilides with human melatonergic affinity is reported. Butyramides 26, 39, 42, 52, 57, and 58 all demonstrated subnanomolar MT2 binding affinity and MT2 selectivity of at least 70-fold over the MT1 receptor. Compound 26 demonstrated full agonism at the MT2 receptor.
