62236-80-0Relevant articles and documents
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.
Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides
Duan, Xin Hong,Xu, Peng
supporting information, p. 19425 - 19431 (2021/11/09)
A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.
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
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
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.
Pyridylmethylamine–Palladium Catalytic Systems: A Selective Alternative in the C?H Arylation of Indole
Perato, Serge,Large, Benjamin,Lu, Qiao,Gaucher, Anne,Prim, Damien
, p. 389 - 392 (2017/02/15)
A highly efficient pyridylmethylamine-Pd alternative catalytic system for the C?H arylation of indole was explored. Variously substituted aryl groups were regio- and chemoselectively installed at the indole nucleus by using barium hydroxide as the base. The method was found to be efficient even in the presence of hindered coupling partners and Pd-reactive bonds.
ORGANIC COMPOUND AND ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE
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Paragraph 0185-0189, (2018/04/03)
The present invention relates to: an organic compound represented by the chemical formula 1; an organic optoelectronic device including the organic compound; and a display device. In the chemical formula 1, X^1, X^2, L^1 to L^3, Ar^1, and R^1 to R^8 are a
Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions
Choi, Isaac,Chung, Hyunho,Park, Jang Won,Chung, Young Keun
supporting information, p. 5508 - 5511 (2016/11/17)
A cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without loss of catalytic activity.
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.
