15657-87-1Relevant academic research and scientific papers
Synthesis of 5-substituted quinolim-8-ols
Nakano, Yoshiharu,Imai, Dai
, p. 1425 - 1428 (1997)
A new preparative procedure for 5-aryl- or 5-decylquinolin-8-ols was developed. The key step of the procedure is the cross coupling of 8-benzyloxy-5-bromoquinoline with arylboronic acid or 9-decyl-9-borabicyclo[3.3.1]nonane (Suzuki reaction). Deprotection
Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines
Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul,Dey, Sayan,Guria, Saikat,Roy, Brindaban,Chattopadhyay, Buddhadeb
supporting information, p. 3333 - 3342 (2021/06/18)
We report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)] 2and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.
Iron-Catalyzed Room Temperature Cross-Couplings of Bromophenols with Aryl Grignard Reagents
Xu, Li-Chen,Liu, Kun-Ming,Duan, Xin-Fang
supporting information, p. 5421 - 5427 (2019/11/14)
Herein we report a room temperature Fe-catalyzed coupling reaction of various bromophenols with aryl Grignard reagents, which exhibits a wide substrate scope and high functional group tolerance. For the first time, the combination of simple Fe(acac)3/PBu3/Ti(OEt)4 has been used as an effective catalyst for the biaryl couplings of bromophenols or their Na or K salts with debromination and etherification side reactions being well suppressed. Various biphenols including natural product garcibiphenyl C as well as pharmaceutical diflunisal and its ethyl ester were facilely synthesized using the present protocol. (Figure presented.).
4-Aryl-8-hydroxyquinolines from 4-chloro-8-tosyloxyquinoline using a Suzuki-Miyaura cross-coupling approach
Heiskanen, Juha P.,Hormi, Osmo E.O.
experimental part, p. 518 - 524 (2009/04/07)
4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki-Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydro
Diboron and triboron compounds based on linear and star-shaped conjugated ligands with 8-hydroxyquinolate functionality: Impact of intermolecular interaction and boron coordination on luminescence
Cui, Yi,Wang, Suning
, p. 6485 - 6496 (2007/10/03)
New 8-R-quinoline functionalized linear and star-shaped conjugated molecules have been synthesized using Suzuki-Miyaura coupling methods (R = MeO, L1-L5; R = CH3OCH2O, L1′-L5′). When treated with HCl, L1′-L5′ are converted readily to
A straightforward methodology for the introduction of aryl and vinyl substituents in the 5 or 7 position of 8-hydroxyquinoline
Babudri, Francesco,Cardone, Antonio,Cioffi, Carla T.,Farinola, Gianluca M.,Naso, Francesco,Ragni, Roberta
, p. 1325 - 1332 (2007/10/03)
A straightforward and general procedure for the introduction of aryl and vinyl substituents in the 5 or 7 position of 8-hydroxyquinoline has been developed. The methodology presented is based upon the Suzuki cross-coupling reaction of aryl or vinyl halide
Effective manipulation of the electronic effects and its influence on the emission of 5-substituted tris(8-quinolinolate) aluminum(III) complexes
Montes, Victor A.,Pohl, Radek,Shinar, Joseph,Anzenbacher Jr., Pavel
, p. 4523 - 4535 (2008/02/07)
The unique electron-transport and emissive properties of tris(8-quinolinolate) aluminum(III) (Alq3) have resulted in extensive use of this material for small molecular organic light-emitting diode (OLED) fabrication. So far, efforts to prepare stable and easy-to-process red/green/blue (RGB)-emitting Alq3 derivatives have met with only a limited success. In this paper, we describe how the electronic nature of various substituents, projected via an arylethynyl or aryl spacer to the position of the highest HOMO density (C5), may be used for effective emission tuning to obtain blue-, green-, and red-emitting materials. The synthetic strategy consists of four different pathways for the attachment of electron-donating and electron-withdrawing aryl or arylethynyl substituents to the 5-position of the quinolinolate ring. Successful tuning of the emission color covering the whole visible spectrum (λ = 450-800 nm) was achieved. In addition, the photophysical properties of the luminophores were found to correlate with the Hammett constant of the respective substituents, providing a powerful strategy with which to predict the optical properties of new materials. We also demonstrate that the electronic nature of the substituent affects the emission properties of the resulting complex through effective modification of the HOMO levels of the quinolinolate ligand.
Red-Green-Blue Emission from Tris(5-aryl-8-quinolinolate)Al(III) Complexes
Pohl, Radek,Montes, Victor A.,Shinar, Joseph,Anzenbacher Jr., Pavel
, p. 1723 - 1725 (2007/10/03)
A simple yet effective strategy for synthesis of 5-aryl-8-quinolinolate-based electroluminophores with tunable emission wavelengths is presented. Two different pathways for the attachment of electron-donating or electron-withdrawing aryl groups to the 5-p
