1666-96-2Relevant articles and documents
PALLADIUM-CATALYZED SYNTHESIS OF QUINOLINES FROM ALLYLIC ALCOHOLS AND o-IODOANILINE
Larock, Richard C.,Kuo, Mann-Yan
, p. 569 - 572 (1991)
The palladium-catalyzed coupling of allylic alcohols and o-iodoaniline provides a convenient, one-step synthesis of quinolines.
An isonitrile-alkyne cascade to di-substituted indoles
Rainier, Jon D.,Kennedy, Abigail R.,Chase, Eric
, p. 6325 - 6327 (1999)
Intramolecular tin and sulfur mediated free-radical cyclizations between an aryl isonitrile and a pendant TMS-substituted alkyne give 2,3- disubstituted indoles from 5-exo-dig cyclization and nucleophilic trapping of the resulting indolenine intermediate.
SBA-15-type organosilica with 4-mercapto-N,N-bis-(3-Si-propyl)butanamide for palladium scavenging and cross-coupling catalysis
El Hankari, Samir,El Kadib, Abdelkrim,Finiels, Annie,Bouhaouss, Ahmed,Moreau, Joel J.E.,Crudden, Cathleen M.,Brunel, Daniel,Hesemann, Peter
, p. 8984 - 8994 (2011)
This work describes the synthesis of novel functional silica materials with difunctional thiol-amide substructures and featuring regular architectures on a mesoscopic level. The functional materials were synthesised by both one-pot co-condensation and post-grafting approaches. The thiol groups confined in the matrix were found to be efficient for palladium entrapment, leading to highly active and reusable heterogeneous catalysts for Sonogashira and Suzuki-Miyaura cross-coupling reactions. This work evidences the crucial role of both the thiol precursor and the condensation degree of the silica scaffold in view of the design of stable and reusable tailor-made mesoporous catalytic silica materials.
Suzuki-miyaura cross-coupling reactions in a Solkane365/227/ethanol blend at ambient temperature
Xu, Xiu-Hua,Azuma, Ayaka,Kusuda, Akihiro,Tokunaga, Etsuko,Shibata, Norio
, p. 1504 - 1508 (2012)
An environmentally benign solvent system, Solkane365/227/ethanol blend, was developed for Suzuki-Miyaura cross-coupling reactions of aryl boronic acids and aryl halides. The reaction is quite general and gives excellent yields for various aryl, heteroaryl, and fluoroaryl boronic acids or halides. Interestingly, this system also allows the synthesis of polyaryls.
Imidazolium supported palladium-chloroglycine complex: Recyclable catalyst for Suzuki-Miyaura coupling reactions
Karthikeyan, Parasuraman,Vanitha, Arumugam,Radhika, Pachaiappan,Suresh, Kannan,Sugumaran, Arunachalam
, p. 7193 - 7197 (2013)
1-Glycyl-3-methyl imidazolium chloride-palladium(II) complex [[Gmim]Cl-Pd(II)] was found to be a catalyst for the Suzuki-Miyaura reaction with excellent yields with high turnover number (6.5 × 102-9.4 × 102).
PEPPSI-Pd-NHC catalyzed Suzuki-Miyaura cross-coupling reactions in aqueous media
Kalo?lu, Nazan,?zdemir, ?smail
, p. 2306 - 2313 (2019)
A series of unsymmetrical 1,3-disubstituted benzimidazolium chlorides were synthesized as N-heterocyclic carbene (NHC) precursors. These compounds were used to synthesize of the PEPPSI-type palladium NHC complexes. The structures of all compounds were cha
Pd Nanoparticles Dispersed on ZrIV Organophosphonate: A Robust and Reusable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions
Borah, Suchibrata,Mishra, Shashank,Cardenas, Luis,Gogoi, Nayanmoni
, p. 751 - 758 (2018)
A mesoporous zirconium(IV) phosphonate was synthesized by the hydrothermal reaction of ZrOCl2·8H2O with a trisphosphonic acid ligand, mesityl-1,3,5-tris(methylenephosphonic acid). Treatment of the mesoporous ZrIV phosphonate framework with Pd(OAc)2 and subsequent reduction produced a nanocomposite where Pd nanoparticles of average size ca. 7–8 nm were found to be homogeneously and abundantly dispersed over the phosphonate framework. The composite acts as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross coupling reaction of aryl bromides with aryl boronic acids.
Copper-catalyzed synthesis of substituted quinolines via C-N coupling/condensation from ortho -acylanilines and alkenyl iodides
Kong, Lingkai,Zhou, Yuanyuan,Huang, He,Yang, Yang,Liu, Yuanyuan,Li, Yanzhong
, p. 1275 - 1278 (2015)
An efficient cascade copper-catalyzed intermolecular Ullmann-type C-N coupling/enamine condensation reaction is described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines in good to excellent yields.
Reusable polymer-supported palladium catalysts: An alternative to tetrakis(triphenylphosphine)palladium in the suzuki cross-coupling reaction
Fenger, Isabelle,Le Drian, Claude
, p. 4287 - 4290 (1998)
The Suzuki cross-coupling reaction of a boronic acid and a bromoaromatic requires palldium catalysis. Almost identical yields were obtained in the usual conditions, with 30 mequiv. of Pd(PPh3)4, and with 2 mequiv of a polymer-supported catalyst, which was easily prepared in two steps from Merrified polymer. Recovery and reuse of the catalyst is easy, and only 0.60% of the initial amount of palladium is lost during a reaction.
Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines
Yang, Tonglin,Nie, Zhi-Wen,Su, Miao-Dong,Li, Hui,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
, p. 15228 - 15241 (2021/10/25)
An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.
