22072-89-5Relevant academic research and scientific papers
Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
, 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
Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles
Zhou, Naifu,Zhao, Junhao,Sun, Chengbo,Lai, Yuqin,Ruan, Zhixiong,Feng, Pengju
, p. 16059 - 16067 (2021/10/01)
A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.
Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group
Camp, Clément,Canivet, Jér?me,Clot, Eric,Demarcy, Clément,Mohr, Yorck,Quadrelli, Elsje Alessandra,Renom-Carrasco, Marc,Thieuleux, Chloé,Wisser, Florian M.
, p. 2713 - 2719 (2020/03/11)
A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 a
Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Br?nsted Acid
Kathe, Prasad M.,Caciuleanu, Alexandru,Berkefeld, Andreas,Fleischer, Ivana
, p. 15183 - 15196 (2020/11/30)
We disclose a nickel/Br?nsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.
Metal-free and regiospecific synthesis of 3-arylindoles
Xie, Wenlai,Xu, Chuangchuang,Xu, Jiaxi
, p. 2661 - 2671 (2020/04/17)
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri
Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
, p. 3085 - 3090 (2019/08/07)
Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism
O'Brien, Connor J.,Droege, Daniel G.,Jiu, Alexander Y.,Gandhi, Shivaani S.,Paras, Nick A.,Olson, Steven H.,Conrad, Jay
, p. 8926 - 8935 (2018/07/05)
The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.
Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles
Yang, Rui,Yu, Jin-Tao,Sun, Song,Zheng, Qingheng,Cheng, Jiang
supporting information, p. 445 - 448 (2017/01/11)
A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.
Metal-free, C-H arylation of indole and its derivatives with aryl diazonium salts by visible-light photoredox catalysis
Zhang, Ying-Peng,Feng, Xiao-Long,Yang, Yun-Shang,Cao, Bi-Xia
supporting information, p. 2298 - 2302 (2016/05/10)
In this Letter, we present the Rhodamine B catalyzed direct C-H arylation of indole with aryl diazonium salts. This method only requires green light and room temperature.
