100381-45-1Relevant articles and documents
RhIII-Catalyzed C-H Activation with Pyridotriazoles: Direct Access to Fluorophores for Metal-Ion Detection
Kim, Ju Hyun,Gensch, Tobias,Zhao, Dongbing,Stegemann, Linda,Strassert, Cristian A.,Glorius, Frank
, p. 10975 - 10979 (2015)
The first C-H bond activation with pyridotriazoles as coupling partners is presented using a RhIII catalyst. The pyridotriazoles can be used as new carbene precursors in C-H activation for direct access to novel fluorescent scaffolds. These tunable fluorophores can be applied for the detection of metal ions.
Electrochemical cross-coupling between 2-halopyridines and aryl or heteroaryl halides catalysed by nickel-2,2'-bipyridine complexes
Gosmini, Corinne,Lasry, Sarah,Nedelec, Jean-Yves,Perichon, Jacques
, p. 1289 - 1298 (1998)
2-Arylpyridines can be obtained in good to high yields by electrochemical reductin using the sacrificial anode process and catalysis by nickel-2,2'-bipyridine (bpy) complexes. In a first approach functionalized arylzinc species are prepared in DMF as solvent by electrolytic reduction of the corresponding aryl-bromides or -chlorides in the presence of ZnBr2 and Ni(II)-bpy complexes and then coupled with 2-chloropyridine. In a second approach the cross-coupling occurs from the electrochemical reduction of a stoichiometric mixture of an aryl halide and 2-halopyridine in DMF in the presence of NiBr2bpy as catalyst.
Kumada coupling of aryl, heteroaryl, and vinyl chlorides catalyzed by amido pincer nickel complexes
Liu, Ning,Wang, Zhong-Xia
, p. 10031 - 10038 (2011)
A series of amido pincer complexes of nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer nickel complexes tested are active catalysts for the cross-coupling of aryl, heteroaryl, and vinyl chlorides with aryl Grignard reagents. The reactions can proceed at room temperature and tolerate functional groups in aryl chlorides with the aid of LiCl and ZnCl2 additives (Figure presented).
Catalytic Electrophilic C-H Silylation of Pyridines Enabled by Temporary Dearomatization
Wübbolt, Simon,Oestreich, Martin
, p. 15876 - 15879 (2015)
A C-H silylation of pyridines that seemingly proceeds through electrophilic aromatic substitution (SEAr) is reported. Reactions of 2- and 3-substituted pyridines with hydrosilanes in the presence of a catalyst that splits the Si-H bond into a hydride and a silicon electrophile yield the corresponding 5-silylated pyridines. This formal silylation of an aromatic C-H bond is the result of a three-step sequence, consisting of a pyridine hydrosilylation, a dehydrogenative C-H silylation of the intermediate enamine, and a 1,4-dihydropyridine retro-hydrosilylation. The key intermediates were detected by 1H NMR spectroscopy and prepared through the individual steps. This complex interplay of electrophilic silylation, hydride transfer, and proton abstraction is promoted by a single catalyst.
Cobalt(III)-Catalyzed Directed C-H Coupling with Diazo Compounds: Straightforward Access towards Extended π-Systems
Zhao, Dongbing,Kim, Ju Hyun,Stegemann, Linda,Strassert, Cristian A.,Glorius, Frank
, p. 4508 - 4511 (2015)
The first highly efficient and scalable cobalt-catalyzed directed C-H functionalization with carbene precursors is presented. This methodology provides a modular route towards a new class of conjugated polycyclic hydrocarbons with tunable emission wavelengths both in solution and in the solid state.
New polystyrene-supported stable source of 2-pyridylboron reagent for Suzuki couplings in combinatorial chemistry
Gros, Philippe,Doudouh, Abdelatif,Fort, Yves
, p. 6239 - 6241 (2004)
The first stable polystyrene-supported 2-pyridylboron reagent has been prepared and involved in Suzuki-Miyaura couplings. Very efficient reactions have been obtained with clean release of target coupling products providing a new tool for combinatorial chemistry.
Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach
Bartolomeu, Aloisio De A.,Brocksom, Timothy J.,De Oliveira, Kleber T.,No?l, Timothy,Silva, Rodrigo C.
, (2019/08/26)
A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96percent. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.
Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
Yang, Bo,Wang, Zhong-Xia
, p. 6220 - 6223 (2017/11/24)
Cross-coupling of (hetero)arylthiols with arylzinc reagents via C-S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.
Cobalt-catalyzed C-H cyanation of (Hetero)arenes and 6-Arylpurines with N -cyanosuccinimide as a new cyanating agent
Pawar, Amit B.,Chang, Sukbok
supporting information, p. 660 - 663 (2015/03/04)
A cobalt-catalyzed C-H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.
General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
supporting information, p. 5901 - 5905 (2015/03/30)
A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
