107734-06-5Relevant academic research and scientific papers
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.
ZnCl2 and Pd/C catalyzed synthesis of 2-substituted indoles
Ahmed, Atiur,Ghosh, Munmun,Sarkar, Pompy,Ray, Jayanta K.
, p. 6691 - 6694 (2013)
A facile, mild, efficient, and copper-free method has been developed for the synthesis of 2-substituted indoles via domino Sonogashira coupling/cyclization reaction catalyzed by ZnCl2 and palladium on carbon with simultaneous formations of C-C and C-N bonds.
"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
Facile synthesis of 2-substituted benzo[: B] furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines
Rong, Zhouting,Gao, Kexin,Zhou, Lei,Lin, Jianyuan,Qian, Guoying
, p. 17975 - 17978 (2019)
A catalytic amount of CuCl and Cs2CO3 was employed to synthesize a variety of 2-substituted benzo[b]furans and indoles by an intramolecular cyclization of 2-alkynyl phenols and tosylanilines. This protocol features mild conditions, h
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.
Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst
Rossy, Cybille,Fouquet, Eric,Felpin, Francois-Xavier
, p. 1426 - 1431 (2013)
This paper describes the preparation of indoles, azaindoles and benzofurans in pure water by using a new heterogeneous Pd-Cu/C catalyst through a cascade Sonogashira alkynylation-cyclization sequence. Details of the optimization studies and the substrate scope are discussed. This procedure allows the preparation of heterocycles with good yields and is tolerant to a wide variety of functional groups.
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
Rhodium(III)-Catalyzed Oxidative Allylic C-H Indolylation via Nucleophilic Cyclization
Sun, Jiaqiong,Wang, Kuan,Wang, Peiyuan,Zheng, Guangfan,Li, Xingwei
, p. 4662 - 4666 (2019)
Reported herein is a mild synthesis of 3-allylindoles via Rh(III)-catalyzed allylic C-H activation of olefins and coupling with o-alkynylanilines. The reaction proceeded via initial nucleophilic cyclization of o-alkynylanilines followed by oxidative coupl
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.
Pd-Catalyzed Enantioselective Tandem C-C Bond Activation/Cacchi Reaction between Cyclobutanones and o-Ethynylanilines
Yang, Wan-Chun,Chen, Xiao-Bing,Song, Kun-Long,Wu, Bin,Gan, Wan-Er,Zheng, Zhan-Jiang,Cao, Jian,Xu, Li-Wen
, p. 1309 - 1314 (2021)
A palladium-catalyzed asymmetric tandem C-C bond activation/Cacchi reaction between cyclobutanones and o-ethynylanilines was reported. The transient chiral σ-alkylpalladium species generated via enantioselective C(sp3)-C(sp2) bond activation of cyclobutanones promotes cyclization of o-ethynylanilines, leading to one-carbon-tethered chiral indanone-substituted indoles. Two C-C bonds and one C-N bond are created with concomitant formation of an all-carbon quaternary stereocenter. Furthermore, a chiral C2-aryl axis can be created in 2,3-disubstituted indole moiety, leading to indanone-substituted indoles with both central and axial stereogenic elements.
