33342-67-5Relevant academic research and scientific papers
Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance
Platon, Mélanie,Wijaya, Novi,Rampazzi, Vincent,Cui, Luchao,Rousselin, Yoann,Saeys, Mark,Hierso, Jean-Cyrille
, p. 12584 - 12594 (2016/08/25)
A constrained binuclear palladium catalyst system affords selective thioetherification of a wide range of functionalized arenethiols with chloroheteroaromatic partners with the highest turnover numbers (TONs) reported to date and tolerates a large variety of reactive functions. The scope of this system includes the coupling of thiophenols with six- and five-membered 2-chloroheteroarenes (i.e., functionalized pyridine, pyrazine, quinoline, pyrimidine, furane, and thiazole) and 3-bromoheteroarenes (i.e., pyridine and furane). Electron-rich congested thiophenols and fluorinated thiophenols are also suitable partners. The coupling of unprotected amino-2-chloropyridines with thiophenol and the successful employment of synthetically valuable chlorothiophenols are described with the same catalyst system. DFT studies attribute the high performance of this binuclear palladium catalyst to the decreased stability of thiolate-containing resting states. Palladium loading was as low as 0.2 mol %, which is important for industrial application and is a step forward in solving catalyst activation/deactivation problems.
C - S coupling using a mixed-ligand Pd catalyst: A highly effective strategy for synthesizing arylthio-substituted heterocycles
Cong, Mei,Fan, Yuting,Raimundo, Jean-Manuel,Xia, Yi,Liu, Yang,Quelever, Gilles,Qu, Fanqi,Peng, Ling
supporting information, p. 17267 - 17272 (2014/01/06)
C - S coupling: A variety of arylthio-substituted heterocycles can be prepared through C - S coupling of the corresponding halide-substituted heterocycles by using a mixed-ligand palladium catalyst, [Pd2(dba) 3]/ Xantphos/CyPF-tBu (see scheme; dba=dibenzylideneacetone). This catalytic system is extremely powerful and efficient, allowing even C - Cl bond activation.
Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles
Rosario, Alisson R.,Casola, Kamila K.,Oliveira, Carla E.S.,Zeni, Gilson
supporting information, p. 2960 - 2966 (2014/03/21)
We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.
Regioselective functionalization of the thiazole scaffold using TMPMgCl?LiCl and TMP2Zn?2MgCl2?2LiCl
Dunst, Cora,Knochel, Paul
experimental part, p. 6972 - 6978 (2011/10/04)
A general method for the synthesis of 2,4,5-trisubstituted thiazoles has been developed. Starting from commercially available 2-bromothiazole, successive metalations using TMPMgCl?LiCl or TMP2Zn?2MgCl 2?2LiCl lead to the correspondin
One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates
Park, Namjin,Park, Kyungho,Jang, Mihee,Lee, Sunwoo
experimental part, p. 4371 - 4378 (2011/07/06)
Aryl sulfides were obtained from the coupling reaction of S-aryl (or S-alkyl) thioacetates and aryl bromides in the presence of palladium catalyst. This reaction method enables the one-pot synthesis of symmetrical and unsymmetrical diaryl sulfides by employing potassium thioacetate with aryl iodides and aryl bromides.
Oxidative amination of heteroaromatic zinc reagents mediated by PhI(OAc)2
Kienle, Marcel,Dunst, Cora,Knochel, Paul
supporting information; experimental part, p. 5158 - 5161 (2009/12/28)
The oxidative amination of functionalized heterocycles has been achieved by using readily available heterocyclic zinc reagents and lithium amides. PhI(OAc)2 proved to be a suitable reagent for this oxidative amination
