19968-61-7Relevant academic research and scientific papers
Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions
Ma, Bei-Bei,Lan, Xiao-Bing,Shen, Dong-Sheng,Liu, Feng-Shou,Xu, Chang
, p. 13 - 22 (2019/06/27)
A highly efficient and practical protocol has been developed for the synthesis of 5-(hetero)arylated thiazole derivatives via an N-heterocyclic carbene palladium (Pd-NHC) complex catalyzed direct C-H arylation reaction. Utilization of this methodology, th
Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles
Maji, Ankur,Singh, Anshu,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik
supporting information, p. 17083 - 17096 (2019/11/26)
A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.
Dehydration Polymerization for Poly(hetero)arene Conjugated Polymers
Mirabal, Rafael A.,Vanderzwet, Luke,Abuadas, Sara,Emmett, Michael R.,Schipper, Derek
supporting information, p. 12231 - 12235 (2018/04/19)
The lack of scalable and sustainable methods to prepare conjugated polymers belies their importance in many enabling technologies. Accessing high-performance poly(hetero)arene conjugated polymers by dehydration has remained an unsolved problem in syntheti
A convenient phosphine-free palladium-catalyzed direct arylation of thiazole under mild aerobic conditions
He, Xiao-Xi,Li, Yan-Fang,Huang, Ju,Shen, Dong-Sheng,Liu, Feng-Shou
, p. 58 - 66 (2015/12/30)
A series of bulky amine palladium complexes {[(Ar-NH2)2PdCl2]} were synthesized and characterized. The catalytic activity of the palladium complexes was evaluated via the direct C-H arylation of thiazoles with aryl bromide
Pd/Cu-cocatalyzed reigoselective arylation of thiazole derivatives at 2-position under ligand-free conditions
Gu, Jian,Cai, Chun
, p. 56311 - 56315 (2015/07/15)
An efficient protocol for regioselective arylation of thiazole derivatives at the 2-position via palladium- and copper-catalyzed C-H bond activation under ligand-free conditions has been developed. The reaction proceeds smoothly with 1% palladium catalyst in the presence of 20% Cu(TFA)2 to furnish the desired products. The direct C-H arylation and no ligand made this method synthetically useful for the arylation of thiazoles at the 2-position.
Reigoselective arylation of thiazole derivatives at 5-position via Pd catalysis under ligand-free conditions
Liu, Xiang-Wei,Shi, Jiang-Ling,Yan, Jia-Xuan,Wei, Jiang-Bo,Peng, Kun,Dai, Le,Li, Chen-Guang,Wang, Bi-Qin,Shi, Zhang-Jie
supporting information, p. 5774 - 5777 (2013/12/04)
An efficient regioselective arylation of thiazole derivatives via Pd-catalyzed C-H activation is reported. The transformation was hypothesized through a Pd(0/II) catalytic cycle in the absence of special ligand sets. This method provided an efficient proc
Palladium-catalyzed decarboxylative cross-coupling reaction between heteroaromatic Carboxylic acids and Aryl halides
Bilodeau, Francois,Brochu, Marie-Christine,Guimond, Nicolas,Thesen, Kris H.,Forgione, Pat
experimental part, p. 1550 - 1560 (2010/06/12)
"Chemical Equation Presented" A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this transformation are reported. Mechanistic evidence is also disclosed that sheds light on possible reaction pathways.
Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners
Forgione, Pat,Brochu, Marie-Christine,St.-Onge, Miguel,Thesen, Kris H.,Bailey, Murray D.,Bilodeau, Francois
, p. 11350 - 11351 (2007/10/03)
Aryl-substituted five-membered heteroaromatics have attracted great interest over the past years due to their presence in a large number of pharmaceuticals and natural products. Recently, an advance in the preparation of these scaffolds was achieved by employing a C-H functionalization strategy. This method allows easy access to these biaryl motifs by precluding the necessity of preparing specific coupling partners, although poor regioselectivity is sometimes observed when more than one reactive C-H is present on the substrate. In an effort to circumvent this liability, we envisioned the use of a carboxylic acid moiety as a blocking group that could be later functionalized or removed. Remarkably, the coupling was found to occur exclusively at the position previously occupied by the acid, even in the presence of a reactive C-H group. This selective transformation was also found to proceed with other heteroaromatic carboxylic acids, allowing for the preparation of a variety of aryl-substituted heteroaromatics that would be difficult to obtain via other methods. Copyright
Mechanism of Base-catalysed Hydrogen-Deuterium Exchange in Thiazolium Ion: Evidence for the Involvement of a Tetrahedral Intermediate
Karimian, Khashayar,Mohtarami, Fatemeh,Askari, Massoud
, p. 1538 - 1543 (2007/10/02)
The mechanism of base-catalysed hydrogen-deuterium exchange of 2-H in the thiazolium ion has been examined by 1H n.m.r. spectroscopy, using small and sterically hindered nucleophiles.Rapid H-D exchange is observed in Me2SO in the cases of 3,4,5-trimethyl- (1), 3-methyl-4,5-diphenyl- (2), 3,5-dimethyl-4-phenyl- (3), and 3,4-dimethyl-5-phenyl-thiazolium iodide (4), when small nucleophiles (KOD-D2O or KOCD3-DOCD3; 0.016M; 25 deg C) are employed.Utilization of a hindered nucleophile however results in a slow exhange of 2-H in (1), (3), and (4), concomitant with H-D exchange of the 4- and 5-methyl exchange of 2-H is detected in the case of (2) with the hindered nucleophile.These observations are ascribed to the formation of a tetrahedral intermediate as a prerequisite of the exchange reaction.
