- NBE-Controlled Palladium-Catalyzed Interannular Selective C-H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2-Acetamides
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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.
- Li, Wenguang,Chen, Wenqi,Zhou, Bang,Xu, Yankun,Deng, Guobo,Liang, Yun,Yang, Yuan
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supporting information
p. 2718 - 2722
(2019/04/16)
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- Copper-Catalyzed Diphenylation of P(O)-OH Bonds with Cyclic Diaryliodonium Salts
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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.
- Wang, Gang,Xiong, Biquan,Zhou, Congshan,Liu, Yu,Xu, Weifeng,Yang, Chang-An,Tang, Ke-Wen,Wong, Wai-Yeung
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p. 4365 - 4374
(2019/11/29)
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- Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2
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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.
- Gao, Yuzhen,Cai, Zhihua,Li, Shangda,Li, Gang
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supporting information
p. 3663 - 3669
(2019/05/17)
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- Palladium-catalyzed interannular meta-C-H arylation
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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
- Ling, Peng-Xiang,Chen, Kai,Shi, Bing-Feng
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supporting information
p. 2166 - 2169
(2017/02/19)
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- Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C-H Activation and Double C-C Bond Formation
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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.
- Zhang, Yanghui,Pan, Shulei,Jiang, Hang,Zhang, Yu,Chen, Dushen
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supporting information
p. 5192 - 5195
(2016/11/02)
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- Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant
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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.
- Liao, Lian-Yan,Liu, Kun-Ming,Duan, Xin-Fang
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p. 9856 - 9867
(2015/11/03)
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- N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling
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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).
- 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
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p. 6549 - 6558
(2015/09/07)
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- Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
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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.
- Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 1597 - 1600
(2015/03/30)
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- One-pot cascade approach to phenanthridine-fused quinazoliniminiums from heteroenyne-allenes
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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.
- Alawode, Olajide E.,Naganaboina, Vijaya Kumar,Liyanage, Thakshila,Desper, John,Rayat, Sundeep
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p. 1494 - 1497
(2014/04/03)
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- Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
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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.
- Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 2892 - 2895
(2014/06/23)
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- Ruthenium-catalyzed regioselective C-H alkenylation directed by a free amino group
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The ruthenium-catalyzed alkenylation reactions of 2-aminobiphenyls and cumylamine proceed smoothly to produce the corresponding regioselectively alkenylated products. These reactions involve a C-H bond cleavage directed by their free amino groups.
- Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 3990 - 3993
(2013/09/02)
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- I -PrI acceleration of Negishi cross-coupling reactions
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(Figure presented) The Negishi cross-coupling of arylzinc reagents with various bromoanilines is accelerated by the presence of i-PrI (1 equiv) and furnished the expected biaryls within 5-12 min reaction time at 25 °C. Arylzinc reagents can also be cross-coupled under these conditions with a range of aryl bromides bearing an enolizable ester or acidic benzylic protons.
- Kienle, Marcel,Knochel, Paul
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supporting information; experimental part
p. 2702 - 2705
(2010/08/20)
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- Rh2(II)-catalyzed synthesis of carbazoles from biaryl azides
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An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.
- Stokes, Benjamin J.,Jovanovic, Brankica,Dong, Huijun,Richert, Kathleen J.,Riell, Ryan D.,Driver, Tom G.
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supporting information; experimental part
p. 3225 - 3228
(2009/08/07)
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