- Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines
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A facile and efficient approach for the synthesis of the CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method has demonstrated low cataly
- Zhang, Zi-Qi,Xu, Yi-Hao,Dai, Jing-Cheng,Li, Yan,Sheng, Jie,Wang, Xi-Sheng
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p. 2194 - 2198
(2021/04/05)
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- A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones
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The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.
- Dai, Ning,Hu, Weican,Qian, Guoying,Rong, Zhouting
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supporting information
p. 3286 - 3290
(2020/04/21)
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- Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
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An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
- He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
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p. 9559 - 9563
(2019/11/21)
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- Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization
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A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.
- Stubbs, James M.,Bridge, Benjamin J.,Blacquiere, Johanna M.
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p. 7928 - 7937
(2019/06/13)
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- Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines
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A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy
- Ye, Yibin,Cheung, Kelvin Pak Shing,He, Lisi,Tsui, Gavin Chit
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supporting information
p. 1676 - 1679
(2018/03/23)
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- Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
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The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
- Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
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p. 3402 - 3405
(2017/07/15)
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- A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
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The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
- Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
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p. 2127 - 2133
(2016/02/18)
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- One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
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A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
- Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
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p. 10987 - 10999
(2016/11/28)
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- Flexible and practical synthesis of 3-oxyindoles through gold-catalyzed intermolecular oxidation of o-ethynylanilines
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A novel gold-catalyzed intermolecular oxidation of o-ethynylanilines has been developed. A range of functionalized 3-oxyindoles are readily accessed by utilizing this strategy. Importantly, this gold-catalyzed oxidative process outcompetes the typical ind
- Shu, Chao,Li, Long,Xiao, Xin-Yu,Yu, Yong-Fei,Ping, Yi-Fan,Zhou, Jin-Mei,Ye, Long-Wu
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p. 8689 - 8692
(2014/07/22)
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- AMPHIPATHIC AND OTHER DOUBLE-SIDED ALPHA-HELIX MIMETICS BASED ON A 1,2-DIPHENYLACETYLENE SCAFFOLD
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Small-molecule scaffolds based on 1,2-diphenylacetylene that accurately replicate the spatial and angular projections of several side chains on both faces of an α-helix, specifically the i and i+7 side chains on one face, and the i and i+2 side chains on the other. The amphipathic α-helix mimetic can be used to disrupt disease-promoting protein-protein interactions that are mediated by α-helices.
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Page/Page column
(2014/09/29)
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- Amphipathic α-helix mimetics based on a 1,2-diphenylacetylene scaffold
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In order to mimic amphipathic α-helices, a novel scaffold based on a 1,2-diphenylacetylene was designed. NMR and computational modeling confirmed that an intramolecular hydrogen bond favors conformations of the 1,2-diphenylacetylene that allow for accurat
- Jung, Kwan-Young,Vanommeslaeghe, Kenno,Lanning, Maryanna E.,Yap, Jeremy L.,Gordon, Caryn,Wilder, Paul T.,Mackerell, Alexander D.,Fletcher, Steven
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p. 3234 - 3237
(2013/07/26)
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- Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts
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An efficient methodology is described and exploited for the preparation of differently substituted indoles and azaindoles via microwave-assisted cycloisomerization in water of 2-alkynylanilines and alkynylpyridinamines, which is promoted by catalytic amounts of neutral or basic salts or by stoichiometric weak organic bases. Good to high yields in the cyclization can be achieved for a variety of 2-amino(hetero)aryl alkynes. Reactions are run without any added metal catalyst. A comparison with the cycloisomerization conducted under conventional heating is also described. An efficient methodology is described for the preparation of differently substituted 1H-indoles and 1H-azaindoles via microwave-assisted cycloisomerization in water of 2-alkynylanilines and alkynylpyridinamines, promoted by catalytic amounts of neutral or basic salts or by weak organic bases.
- Carpita, Adriano,Ribecai, Arianna,Stabile, Paolo
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experimental part
p. 7169 - 7178
(2010/10/01)
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