4253-80-9Relevant academic research and scientific papers
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Tetramethylammonium fluoride tetrahydrate-mediated transition metal-free coupling of aryl iodides with unactivated arenes in air
Nozawa-Kumada, Kanako,Nakamura, Kosuke,Kurosu, Satoshi,Iwakawa, Yuki,Denneval, Charline,Shigeno, Masanori,Kondo, Yoshinori
, p. 1042 - 1045 (2019/10/02)
Biaryls are important compounds with widespread applications in many fields. Tetramethylammonium fluoride tetrahydrate was found to promote the biaryl coupling of aryl iodides bearing electron-withdrawing substituents with unactivated arenes. The reaction takes place at temperatures between 100 and 150°C and can be applied to a wide range of aromatic and heteroaromatic rings, affording the products in moderate to high yields. The reaction does not require strong bases or expensive additives that are employed in the existing methods and can be conducted in air and moisture without any precautions.
N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling
Lai, Mei-Jung,Lee, Hsueh-Yun,Chuang, Hsun-Yueh,Chang, Li-Hsun,Tsai, An-Chi,Chen, Mei-Chuan,Huang, Han-Lin,Wu, Yi-Wen,Teng, Che-Ming,Pan, Shiow-Lin,Liu, Yi-Min,Mehndiratta, Samir,Liou, Jing-Ping
, p. 6549 - 6558 (2015/09/07)
A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).
COMPOUNDS AND METHODS FOR TREATING CANCERS
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Paragraph 0124; 0125, (2014/10/04)
Provided are carbazole and carbazole-like compounds (e.g., pyridoindole and pyrrolodipyridine) compounds, that can be used to selectively kill cancer cells, specifically androgen-receptor expressing prostate cancer cells. Also provided is a method of treating AR-positive prostate cancer in a subject diagnosed with or suspected of having AR positive or negative cancer, comprising administering an effective amount of a carbazole and carbazole-like compound to said subject.
Copper-catalyzed decarboxylation of aromatic carboxylic acids: En route to milder reaction conditions
Cahiez, Gerard,Moyeux, Alban,Gager, Olivier,Poizat, Mael
supporting information, p. 790 - 796 (2013/04/10)
The copper-catalyzed decarboxylation of carboxylic aromatic acids has been advantageously achieved by using aliphatic amines like tetramethylethylenediamine (TMEDA) or hexamethylenetetraamine (HMTA) as ligands instead of the aromatic heterocyclic amines (quinoline, phenanthroline) used until now. The improvement is significant since the reaction can be performed at a lower temperature (ca. 50 °C less) and the reaction time is clearly shorter (15 min instead of 12 to 24 h). Copyright
Efficient diphosphane-based catalyst for the palladium-catalyzed suzuki cross-coupling reaction of 3-pyridylboronic acids
Fu, Xing-Li,Wu, Lei-Lei,Fu, Hai-Yan,Chen, Hua,Li, Rui-Xiang
experimental part, p. 2051 - 2054 (2009/09/06)
A highly active catalyst system derived from PdCl2 and 2,2',6,6'- tetramethoxy-4,4'-bis(diphenylphosphanyl)-3,3'-bi- pyridine (P-Phos) has been developed for the Suzuki cross- coupling reaction of pyridylboronic acid with a variety of aryl halides in good to excellent yields, even in the presence of hindered and functional groups. In addition, P-Phos also exhibited high activity in the palladium-catalyzed Suzuki reaction of 2,6-dimethoxypyridylboronic acid in excellent yields with a fast rate. The steric and electronic effects of the P- Phos-palladium complex to this cross-coupling reaction were also discussed.
Synthesis of biaryls and aryl ketones via microwave-assisted decarboxylative cross-couplings
Goossen, Lukas J.,Linder, Bettina Zimmermanns Christophe,Rodriguez, Nuria,Lange, Paul P.,Hartung, Jens
experimental part, p. 2667 - 2674 (2009/12/31)
A protocol for the microwave-assisted decarboxylative cross-couplings of carboxylic acid salts with aryl halides has been developed that allows the synthesis of various biaryls and aryl ketones in high yields. After careful adaptation of the bimetallic ca
Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates
Goossen, Lukas J.,Zimmermann, Bettina,Knauber, Thomas
experimental part, p. 7103 - 7106 (2009/04/12)
(Chemical Equation Presented) Even non-activated aryl chlorides undergo decarboxylative cross-coupling reactions in the presence of a catalyst system generated in situ from CuI, 1,10-phenanthroline, PdI2, and di(tert-butyl)biphenylphosphane. The new catalyst is useful for both the synthesis of biaryl compounds from aromatic carboxylates and the synthesis of aryl ketones from salts of α-ketocarboxylic acids (see scheme; FG=functional group; R=aryl, alkyl).
Method For Decarboxylating C-C Cross-Linking Of Carboxylic Acids With Carbon Electrophiles
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Page/Page column 8-9, (2008/12/07)
The invention relates to a method for decarboxylating C—C bond formation by reacting carboxylic salts with carbon electrophiles in the presence of transition metal compounds as catalysts. The method represents a decarboxylating C—C bond formation of carboxylic acid salts with carbon electrophiles, wherein the catalyst contains two transition metals and/or transition metal compounds, from which one is present, preferably, in the oxidation step, which are different from each other by one unit, and catalyzes a radical decarboxylation which is absorbed during the second oxidation steps, which are different from each other by two units and catalyzes the two electron processes of a C—C bond formation reaction.
Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides
Goossen, Lukas J.,Rodriguez, Nuria,Melzer, Bettina,Linder, Christophe,Deng, Guojun,Levy, Laura M.
, p. 4824 - 4833 (2008/01/27)
A new strategy for the regiospecific construction of unsymmetrical biaryls is presented, in which easily available salts of carboxylic acids are decarboxylated in situ to give arylmetal species that serve as the nucleophilic component in a catalytic cross-coupling reaction with aryl halides. The catalyst system consists of a copper phenanthroline complex that mediates the extrusion of CO2 from aromatic carboxylates to generate arylcopper species, and a palladium complex that catalyzes the cross-coupling of these intermediates with aryl halides. This bimetallic system allows the direct coupling of various aryl, heteroaryl, or vinyl carboxylic acids with aryl or heteroaryl iodides, bromides, or chlorides at 160°C in the presence of a mild base such as potassium carbonate. The present scope and potential economic impact of the reaction are demonstrated by the synthesis of 42 biaryls, some of which are of substantial industrial relevance. Remaining challenges and future perspectives of the new transformation are discussed.
