1504-16-1Relevant articles and documents
Direct palladium-catalyzed C-3 arylation of indoles
Zhang, Zhiqiang,Hu, Zhizhi,Yu, Zhixiao,Lei, Peng,Chi, Haijun,Wang, Yue,He, Ren
, p. 2415 - 2419 (2007)
An efficient protocol for palladium-catalyzed direct C-3 arylation of indoles containing unprotected heterocyclic nitrogen atom has been developed.
A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhanced conditions
Karuvalam, Ranjith P.,Haridas, Karickal R.,Sajith, Ayyiliath M.,Muralidharan, Arayambath
, p. 5126 - 5129 (2013)
A facile access to differently substituted indoles using palladium catalyzed annulation reactions under microwave enhanced conditions has been achieved. A highly active and efficient catalytic system PdCl 2/(A-taphos) for the synthesis of indole via palladium catalyzed ring annulation of ortho iodo anilines and aldehydes has been developed.
Mechanistic Study of Direct Arylation of Indole Using Differential Selectivity Measurements: Shedding Light on the Active Species and Revealing the Key Role of Electrophilic Substitution in the Catalytic Cycle
Kurokhtina, Anna A.,Larina, Elizaveta V.,Yarosh, Elena V.,Lagoda, Nadezhda A.,Schmidt, Alexander F.
, p. 2054 - 2063 (2018)
Differential selectivity of the direct arylation of indole with aryl halides under competing and noncompeting conditions with a varying set of reaction parameters was determined using phase trajectories. The results described herein allow for conclusions to be drawn regarding the character of active complexes (cationic, neutral, or anionic) as well as realization of the indole electrophilic substitution in the catalytic cycle using the ligand-free catalytic system.
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Isomura et al.
, p. 664 (1977)
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Development of Pd Supported Catalysts Using Thiol-Functionalized Mesoporous Silica Frameworks: Application to the Chemo- and Regioselective C-3 Arylation of Free-Indole
Renom Carrasco, Marc,Khodja, Walid,Demarcy, Clément,Veyre, Laurent,Camp, Clément,Thieuleux, Chloé
, p. 814 - 820 (2021)
We report here the development of Pd-supported catalysts for the selective C-3 arylation of free-indole using thiol-functionalized silica supports to anchor the palladium centers. The palladium (II) complex, Pd(OAc)2, was efficiently loaded into various thiol-functionalized mesostructured silicas at room temperature. These materials exhibit different contents of surface SH groups (0.3 to 1.8 SH/nm2) and various SH/Pd molar ratios from 6 to 65. It was found that the catalysts containing the most isolated surface SH groups (0.3 SH/nm2) and the highest loading of Pd were the most active, reaching 70 % of conversion, 1400 as turnover numbers and 100 % selectivity in the C-3 arylated product using only 0.05 mol % of Pd. However, a leaching of active Pd species (1.7 ppm) was detected. The best compromise was found for a specific solid containing isolated surface thiol groups (0.3 SH/nm2) and a very low loading of Pd (SH/Pd=65). It exhibited a high TON (608) with a very low Pd leaching of 0.5 ppm in the course of the catalytic reaction. These results thus illustrate that both surface SH sites isolation and concentration, as well as the SH/Pd molar ratio are key parameters to access high catalytic performances and very low leaching of metal during catalysis.
Efficient synthesis of N-methoxyindoles via alkylative cycloaddition of nitrosoarenes with alkynes
Penoni, Andrea,Palmisano, Giovanni,Broggini, Gianluigi,Kadowaki, Ayako,Nicholas, Kenneth M.
, p. 823 - 825 (2006)
N-Methoxyindoles are produced in moderate to excellent yields from the reaction between nitrosoarenes and alkynes in the presence of K 2CO3/(CH3)2SO4. Terminal alkynes with conjugating substituents af
Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
supporting information, p. 12309 - 12312 (2021/12/07)
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
Synthesis and antimycobacterial activity of 3-phenyl-1h-indoles
Abbadi, Bruno Lopes,Basso, Luiz Augusto,Bizarro, Cristiano Valim,Dornelles, Maiele,Duarte, Lovaine,Etchart, Renata Jardim,Lourega, Rogério Vescia,Macchi, Fernanda Souza,Machado, Pablo,Neves, Christiano Ev,Perelló, Marcia Alberton,Rambo, Raoní S.,Silva, Fernanda Fries,Sperotto, Nathalia
, (2021/08/31)
Tuberculosis has been described as a global health crisis since the 1990s, with an estimated 1.4 million deaths in the last year. Herein, a series of 20 1H-indoles were synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (Mtb) g