365-06-0Relevant academic research and scientific papers
NBE-Controlled Palladium-Catalyzed Interannular Selective C-H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2-Acetamides
Li, Wenguang,Chen, Wenqi,Zhou, Bang,Xu, Yankun,Deng, Guobo,Liang, Yun,Yang, Yuan
supporting information, p. 2718 - 2722 (2019/04/16)
A novel palladium-catalyzed interannular selective C-H silylation of 1,1′-biaryl-2-acetamides is described. The combination of palladium catalyst with copper oxidant enables meta- or ortho-selective C-H silylation by employing hexamethyldisilane as a trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent silicon-containing 1,1′-biaryl-2-acetamides.
Copper-Catalyzed Diphenylation of P(O)-OH Bonds with Cyclic Diaryliodonium Salts
Wang, Gang,Xiong, Biquan,Zhou, Congshan,Liu, Yu,Xu, Weifeng,Yang, Chang-An,Tang, Ke-Wen,Wong, Wai-Yeung
, p. 4365 - 4374 (2019/11/29)
A copper-catalyzed diphenylation of P(O)?OH bonds with cyclic diaryliodonium salts is described. Valuable 2′-iodo substituted biaryl phosphinic/phosphoric acid esters were obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.
Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2
Gao, Yuzhen,Cai, Zhihua,Li, Shangda,Li, Gang
supporting information, p. 3663 - 3669 (2019/05/17)
An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.
Palladium-catalyzed interannular meta-C-H arylation
Ling, Peng-Xiang,Chen, Kai,Shi, Bing-Feng
supporting information, p. 2166 - 2169 (2017/02/19)
The interannular meta-selective C-H arylation of biaryl-2-trifluoroacetamides using Pd(ii)/norbornene catalysis is reported. The installation of a trifluoroacetyl protecting group to tune their electronic properties and binding ability is essential for in
Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C-H Activation and Double C-C Bond Formation
Zhang, Yanghui,Pan, Shulei,Jiang, Hang,Zhang, Yu,Chen, Dushen
supporting information, p. 5192 - 5195 (2016/11/02)
A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C-H activations and double palladium-catalyzed C-C bond formations. A range of unsymmetrically functionalized triphenylenes can be synthesized with the reaction. The approach features readily available starting materials, high atom- and step-economy, and access to various unsymmetrically functionalized triphenylenes.
Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information, p. 1597 - 1600 (2015/03/30)
The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant
Liao, Lian-Yan,Liu, Kun-Ming,Duan, Xin-Fang
, p. 9856 - 9867 (2015/11/03)
The first cobalt-catalyzed oxidative cross-coupling reaction of two aryl metal reagents is described. An equivalent amount of two aryl Grignard or lithium reagents, after mediation by an equivalent amount of simple ClTi(OEt)3, was facilely assembled under the catalysis of 1 mol % of CoCl2/10 mol % of DMPU using oxygen. The cross-couplings between various aryl metal reagents, especially between two structurally similar aryl Grignard reagents, proceeded smoothly and selectively and, thus, provided a highly general and efficient method for the construction of biaryl compounds.
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).
One-pot cascade approach to phenanthridine-fused quinazoliniminiums from heteroenyne-allenes
Alawode, Olajide E.,Naganaboina, Vijaya Kumar,Liyanage, Thakshila,Desper, John,Rayat, Sundeep
supporting information, p. 1494 - 1497 (2014/04/03)
A one-pot cascade method to obtain functionalized phenanthridine-fused quinazoliniminiums from a variety of heteroenyne-allenes is described. This protocol involves formation of C-N and C-C bonds in a single step in the presence of a Lewis acid and trace water to afford pentacyclic title compounds in moderate to good yields.
Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information, p. 2892 - 2895 (2014/06/23)
A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
