107734-06-5Relevant articles and documents
Heterogeneous palladium catalysts applied to the synthesis of 2- and 2,3-functionalised indoles
Djakovitch, Laurent,Dufaud, Veronique,Zaidi, Rabah
, p. 715 - 724 (2006)
Heterogeneous palladium catalysts ([Pd(NH3)4] 2+/NaY and [Pd]/SBA-15) were applied to the synthesis of 2-functionalised indoles, giving generally high conversions and selectivities (>89% yield) using only 1 mol % [Pd]-catalyst under standard reaction conditions (polar solvent, 80°C). For the synthesis of 2,3-functionalised indoles by cross-coupling arylation, the [Pd]/SBA-15 catalyst was found to be particularly interesting, producing the expected compound with =35% yield after 12 days of reaction, which is comparable to the homogeneous catalyst, Pd(OAc)2 (= 48% yield). In the course of the study, the dual reactivity of the indole nucleus was demonstrated: aryl bromides gave clean C-C coupling while aryl iodides led to a clean C-N coupling.
"quick and click" assembly of functionalised indole rings via metal-promoted cyclative tandem reactions
Capitta, Francesca,De Luca, Lidia,Porcheddu, Andrea
, p. 59297 - 59301 (2014)
An efficient and convenient synthesis of a variety of decorated indoles using a three-component tandem metal-catalysed process is described. We propose here a new "synthetic kit" that allows for the "quick and click" assembly of indole rings using readily available, and inexpensive starting materials under environmentally friendly reaction conditions. This journal is
The cooperative FeCl3/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines
Jang, Su San,Youn, So Won
, p. 2200 - 2204 (2016)
A highly regioselective synthesis of 3-arylindoles by using the cooperative FeCl3/DDQ system has been developed. This new protocol represents an attractive route for the synthesis of 3-arylindoles from readily accessible non-indole precursors, β-aryl-substituted 2-styrylanilines, using an inexpensive catalyst and oxidant. Noteworthy is the unique synergetic and synergistic effect of FeCl3 and DDQ on the 1,2-aryl migratory process.
Synthesis and Stabilities of 3-Borylated Indoles
Al-Saedy, Muhannad A. E.,Harrity, Joseph P. A.
, p. 1674 - 1676 (2016)
We report herein that 3-pinacol boronic esters undergo facile protodeborylation in the presence of palladium catalysts and base, and this contributes significantly to the generation of nonborylated indole byproducts in the B2Pin2-med
A facile, mild and efficient one-pot synthesis of 2-substituted indole derivatives catalyzed by Pd(PPh3)2Cl2
Oskooie, Hossien A.,Heravi, Majid M.,Behbahani, Farahnaz K.
, p. 1438 - 1446 (2007)
2-Phenylindoles were prepared by heteroannulation of 2-haloaniline derivatives and phenylacetylene under mild conditions in a one-pot reaction catalyzed by Pd(PPh3)2Cl2.
Palladium-Catalyzed Cascade Heck Cyclization to Access Bisindoles
Yuan, Kai,Liu, Lina,Chen, Jiayi,Guo, Songjin,Yao, Hequan,Lin, Aijun
, p. 3477 - 3481 (2018)
A novel strategy for intercepting the σ-alkylpalladium species generated via a Heck reaction, enabling a palladium-catalyzed cyclization of o-ethynylanilines, has been described. This direct and operationally simple protocol provided a fundamental platform to synthesize bisindoles with high efficiency, involving one C-N bond and two C-C bond formations.
Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam
Bruneau, Alexandre,Gustafson, Karl P. J.,Yuan, Ning,Tai, Cheuk-Wai,Persson, Ingmar,Zou, Xiaodong,B?ckvall, Jan-E.
, p. 12886 - 12891 (2017)
Herein, we report on the utilization of a heterogeneous catalyst, consisting of Pd nanoparticles supported on a siliceous mesocellular foam (Pd0-AmP-MCF), for the synthesis of heterocycles. Reaction of o-iodophenols and protected o-iodoanilines with acetylenes in the presence of a Pd nanocatalyst produced 2-substituted benzofurans and indoles, respectively. In general, the catalytic protocol afforded the desired products in good to excellent yields under mild reaction conditions without the addition of ligands. Moreover, the structure of the reported Pd nanocatalyst was further elucidated with extended X-ray absorption fine-structure spectroscopy, and it was proven that the catalyst could be recycled multiple times without significant loss of activity.
Supported palladium nanoparticles-catalyzed decarboxylative coupling approaches to aryl alkynes, indoles and pyrrolines synthesis
Reddy, C. Bal,Bharti, Richa,Kumar, Sandeep,Das, Pralay
, p. 71117 - 71121 (2016)
The polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed decarboxylative coupling (DC) of arylhalides and alkynyl carboxylic acids was developed for the synthesis of diaryl alkynes. Indole and 3-pyrroline heterocycles were also synthesized from 2-iodo anilines/amino benzocycloheptene bromide and alkynyl carboxylic acids, following a domino decarboxylative coupling-cyclization (DCC) approach under the same catalytic conditions. The combined anchoring and catalytic behaviour of Pd@PS makes the process favourable for the product formation.
Synthesis of 2-substituted indoles by palladium-catalyzed heteroannulation with Pd-NaY zeolite catalysts
Hong, Ki Bum,Lee, Chul Wee,Yum, Eul Kgun
, p. 693 - 697 (2004)
Various 2-substituted indoles were prepared by heteroannulation of o-iodoanilines and terminal alkynes in a one-pot reaction with a Pd(II)-NaY zeolite catalyst. The product formation largely depended on the solvent, base, and reaction temperature. The recycled catalyst showed good reusability in the heteroannulation reaction.
Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites
Cook, Amanda K.,Copéret, Christophe
, p. 1342 - 1345 (2018)
Hydroamination is an atom-economical reaction to form C-N bonds, which are ubiquitous in organic compounds. Hydroamination has seen prolific advancements and has mostly focused on the development of homogeneous catalysts based on lanthanides or transition metals. Here, we have developed silica-supported, site-isolated Zn(II) sites through a combined surface organometallic chemistry (SOMC) and thermolytic molecular precursor (TMP) approach and show that they catalyze the intramolecular hydroamination of alkynes. This material is applicable to a broad range of substrates. On the basis of kinetics and in situ IR spectroscopic studies, we propose that the mechanism involves coordination of the aminoalkyne onto Zn(II) followed by the heterolytic activation of the N-H bond and subsequent cyclization and proton transfer.
Direct C-H amination for indole synthesis from N-Ts-2-Styrylaniline derivatives catalyzed by copper salt
Chen, Di,Mo, Han-Jie,Chen, Ding-Ben,Yang, Jian-Guo
, p. 969 - 972 (2015)
Abstract A direct C-H amination reaction of N-Ts-2-Styrylaniline derivatives to realize the synthesis of indole derivatives was developed in the presence of copper salt. A variety of N-Ts-2-Styrylaniline derivatives were transformed into the corresponding
Accessing Unsymmetrically Linked Heterocycles through Stereoselective Palladium-Catalyzed Domino Cyclization
Arora, Ramon,Lautens, Mark,Rodríguez, José F.,Whyte, Andrew
supporting information, (2021/12/09)
A palladium-catalyzed strategy is presented to synthesize unsymmetrically linked heterocycles within stereoselective tetrasubstituted olefins. This reaction is proposed to occur via a vinyl-PdII intermediate capable of initiating the cyclizatio
DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Zhang, Jingran,Li, Xiaoxian,Li, Xuemin,Shi, Haofeng,Sun, Fengxia,Du, Yunfei
, p. 460 - 463 (2021/01/25)
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
