55968-16-6Relevant academic research and scientific papers
Spectroscopy and photophysics of bifunctional proton donor-acceptor indole derivatives
Vetokhina, Volha,Kijak, Micha?,Lipinska, Teodozja M.,Thummel, Randolph P.,Sepiol, Jerzy,Waluk, Jacek,Herbich, Jerzy
, p. 4898 - 4906 (2013)
We report spectroscopic and photophysical studies of a series of selected indole derivatives in solutions and under supersonic jet isolation conditions. All the compounds can assume two rotameric forms, syn and anti. The bifunctional molecules containing
Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
, p. 9246 - 9250 (2021/12/06)
The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
Chen, Shaomin,Gu, Yanlong,Li, Minghao
, p. 10431 - 10434 (2021/10/12)
Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Cascade annulative π-extension for the rapid construction of carbazole based polyaromatic hydrocarbons
Banerjee, Ankush,Ghosh, Meghna,Kundu, Samrat,Maji, Modhu Sudan,Pal, Shyam Chand
supporting information, p. 5762 - 5765 (2021/06/16)
A Br?nsted acid catalyzed cascade benzannulation strategy for the one-pot synthesis of densely populated poly-aryl benzo[a]carbazole architectures is disclosed from easily affordable fundamental commodities. The efficacy of this technique was further validated via the concise synthesis of structurally unique carbazole based poly-aromatic hydrocarbons. Furthermore, the photo-physical properties of the synthesized compounds are thoroughly investigated.
Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
supporting information, p. 10242 - 10245 (2021/10/12)
Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones
Dong, Chun-Lin,Ding, Xuan,Huang, Lan-Qian,He, Yan-Hong,Guan, Zhi
supporting information, p. 1076 - 1080 (2020/02/15)
A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.
Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles
Long, Han,Xu, Kunhua,Chen, Shanshan,Lin, Jin,Wu, Dan,Wu, Bo,Tian, Xu,Ackermann, Lutz
supporting information, (2019/05/08)
An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.
Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles
Long, Han,Xu, Kunhua,Chen, Shanshan,Lin, Jin,Wu, Dan,Wu, Bo,Tian, Xu,Ackermann, Lutz
supporting information, p. 3053 - 3056 (2019/05/10)
An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.
Palladium-Catalyzed C–C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles
Bellezza, Delia,Noverges, Bárbara,Fasano, Francesco,Sarmiento, Jeymy T.,Medio-Simón, Mercedes,Asensio, Gregorio
, p. 1229 - 1235 (2019/01/04)
The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or commercially available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.
