4253-81-0Relevant academic research and scientific papers
NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 5349 - 5353 (2021/07/21)
A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.
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.
COMPOUNDS AND METHODS FOR TREATING CANCER
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Paragraph 0190; 0364-0366, (2020/12/19)
Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.
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.
Metal complex and OLED (Organic Light Emitting Device) thereof
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Paragraph 0086; 0087; 0088; 0089, (2018/10/19)
The invention discloses a metal complex and an OLED (Organic Light Emitting Device) thereof, and relates to the technical field of organic photoelectric materials. The metal complex has a structure asshown in a formula (I), wherein an electron-rich dinitrogen coordination structure in the structure of the metal complex is beneficial for stabilizing central trivalent metal cations, and meanwhile,electron cloud distribution on metal iridium can also be affected, so that great influence to the photoelectric properties of a whole complex molecule can be generated; a quaternary ring formed by a ligand of the dinitrogen coordination structure and metal has stronger rigidity and is beneficial for reducing unnecessary vibration energy loss and realizing high-efficiency luminescence property. Byregulating substituent groups, the metal complex has better thermal stability and chemical property; by preparing the metal complex into a device and particularly using the metal complex as a doping material, the device has the advantages of low driving voltage and high luminous efficiency and is superior to a commonly used OLED.
Meta-Selective CAr-H Nitration of Arenes through a Ru3(CO)12-Catalyzed Ortho-Metalation Strategy
Fan, Zhoulong,Ni, Jiabin,Zhang, Ao
supporting information, p. 8470 - 8475 (2016/07/26)
The first example of transition metal-catalyzed meta-selective CAr-H nitration of arenes is described. With the use of Ru3(CO)12 as the catalyst and Cu(NO3)2·3H2O as the nitro source, a wide spectrum of arenes bearing diversified N-heterocycles or oximido as the directing groups were nitrated with meta-selectivity exclusively. Mechanism studies have demonstrated the formation of a new 18e-octahedral ruthenium species as a key ortho-CAr-H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic aromatic substitution (SEAr). Moreover, this approach provides a fast-track strategy for atom/step economical synthesis of many useful pharmaceutical molecules.
Rhodium-Catalyzed C-S and C-N Functionalization of Arenes: Combination of C-H Activation and Hypervalent Iodine Chemistry
Wang, Fen,Yu, Xinzhang,Qi, Zisong,Li, Xingwei
supporting information, p. 511 - 516 (2016/01/12)
Rhodium-catalyzed sulfonylation, thioetherification, thiocyanation, and other heterofunctionalizations of arenes bearing a heterocyclic directing group have been realized. The reaction proceeds by initial RhIII-catalyzed C-H hyperiodination of
Aerobic oxidation of PdII to PdIV by active radical reactants: Direct C-H nitration and acylation of arenes via oxygenation process with molecular oxygen
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Yan, Yuepeng,Feng, Peng,Jiao, Ning
, p. 1956 - 1963 (2015/03/14)
A Pd-catalyzed aerobic oxidative C-H nitration and acylation of arenes with simple and readily available tert-butyl nitrite (TBN) and toluene as the radical precursors has been developed. Molecular oxygen is employed as the terminal oxidant and oxygen source to initiate the active radical reactants. Many different directing groups such as pyridine, pyrimidine, pyrazole, pyridol, pyridylketone, oxime, and azo groups can be employed in these novel transformations. The PdII/PdIV catalytic cycle through a radical process is the most likely pathway for these oxidative C-H nitration and acylation reactions.
Facile formation of imidazolinium salt by reaction of corresponding diamine and trimethyl orthoformate in 1,1,1,3,3,3-hexafluoroisopropanol
Usui, Kensuke,Nakada, Masahisa
, p. 1539 - 1551 (2016/11/07)
The preparation of imidazolinium salts, which can be used as precursors of pincer-type N-heterocyclic carbene ligands, is described. The formation of imidazolinium salts under standard conditions is difficult, but they have been successfully synthesized by reaction of the corresponding diamines and trimethyl orthoformate in 1,1,1,3,3,3-hexafluoroisopropanol. The synthesis of new chiral C2 symmetric imidazolinium salts is also described.
Rhodium(III)-catalyzed azidation and nitration of arenes by C-H activation
Xie, Fang,Qi, Zisong,Li, Xingwei
supporting information, p. 11862 - 11866 (2013/11/19)
Getting a handle on it: In the chelation-assisted title reactions in the presence of a hypervalent iodine oxidant, sodium azide and sodium nitrite served as readily available nitrogen sources, and pyridine, pyrimidine, and pyrazole substituents were effic
