5957-84-6Relevant academic research and scientific papers
Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone
Miao, Wenjun,Ni, Chuanfa,Xiao, Pan,Jia, Rulong,Zhang, Wei,Hu, Jinbo
supporting information, p. 711 - 715 (2021/01/26)
A novel nickel-catalyzed reductive cross-coupling between aryl iodides and difluoromethyl 2-pyridyl sulfone (2-PySO2CF2H) enables C(sp2)-C(sp2) bond formation through selective C(sp2)-S bond cleavage, which demonstrates the new reactivity of 2-PySO2CF2H reagent. This method employs readily available nickel catalyst and sulfones as cross-electrophile coupling partners, providing facile access to biaryls under mild reaction conditions without pregeneration of arylmetal reagents.
Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate
Zhang, Shang-Shi,Zheng, Yi-Chuan,Zhang, Zi-Wu,Chen, Shao-Yong,Xie, Hui,Shu, Bing,Song, Jia-Lin,Liu, Yan-Zhi,Zeng, Yao-Fu,Zhang, Luyong
supporting information, p. 5719 - 5723 (2021/08/16)
A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.
Synthesis, structures and photophysical properties of hexacoordinated organosilicon compounds with 2-(2-pyridyl)phenyl groups
Furuta, Shohei,Kuninobu, Yoichiro,Mori, Toshiaki,Sekine, Kohei,Yoshigoe, Yusuke
, p. 3239 - 3242 (2020/05/14)
We synthesised novel hexacoordinated organosilicon compounds with two 2-(2-pyridyl)phenyl groups. Single-crystal X-ray structure analyses indicated that Lewis acid-base interactions exist between the silicon atom and two nitrogen atoms of the pyridine rings, and that hexacoordinated organosilicon compounds have slightly distorted octahedral structures in the solid state. The hexacoordinated organosilicon compounds are stable in air, water, heat, acids, and bases. The fluorescent quantum yield increased dramatically and a significant red-shift of the maximum fluorescence wavelength was observed with the introduction of amino groups on the 2-(2-pyridyl)phenyl aromatic rings. The fluorescence colours of a hexacoordinated organosilicon compound with two amino groups can be switched by protonation and deprotonation (neutralisation) of the amino groups.
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.
Multicomponent Aromatic and Benzylic Mannich Reactions through C?H Bond Activation
Xavier, Tania,Rayapin, Corinne,Le Gall, Erwan,Presset, Marc
supporting information, p. 13824 - 13828 (2019/11/03)
Multicomponent Mannich reactions through C?H bond activation are described. These transformations allowed for the straightforward generation of densely substituted benzylic and homo-benzylic amines in good yields. The reaction involves a reaction between two transient species: an organometallic species, generated by transition-metal-catalyzed sp2 or sp3 C?H bond activation and an in situ generated imine. The use of an acetal as an aldehyde surrogate was found essential for the reaction to proceed. The process could be successfully applied to RhIII-catalyzed sp2 C?H bond functionalization and extended to CuII-catalyzed sp3 C?H bond functionalization.
N-heterocyclic carbene enabled rhodium-catalyzed ortho C(sp2)-H borylation at room temperature
Zhong, Lei,Zong, Zhi-Hong,Wang, Xi-Cun
supporting information, p. 2547 - 2552 (2019/03/27)
We report a rhodium-catalyzed ortho C(sp2)-H borylation of 2-phenylpyridines using commercially available N-heterocyclic carbenes (NHCs) as ligand and pinacolatodiboron (B2pin2) as borylating reagent. The reaction could take place at room temperature, tolerating a wide range of functionalities and affording ortho borylated products in moderate to excellent yields. The current method is also applicable to gram-scale reaction with reduced catalyst loading.
Towards blue emitting monocyclometalated gold(iii) complexes-synthesis, characterization and photophysical investigations
Bachmann, Michael,Fessler, Reto,Blacque, Olivier,Venkatesan, Koushik
supporting information, p. 7320 - 7330 (2019/06/06)
Blue emitting phosphorescent materials with high efficiency and high stability are a key requirement for the wider adoption of organic light emitting devices (OLEDs). In order to achieve triplet derived emission at the higher energy region of the electrom
[2,2′-bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
Salamanca, Vanesa,Toledo, Alberto,Albéniz, Ana C.
supporting information, p. 17851 - 17856 (2019/01/04)
The ligand [2,2′-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.
Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor
Fabry, David C.,Ho, Yee Ann,Zapf, Ralf,Tremel, Wolfgang,Panth?fer, Martin,Rueping, Magnus,Rehm, Thomas H.
supporting information, p. 1911 - 1918 (2017/06/09)
Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.
Photoluminescence and electroluminescence of four platinum complexes with trifluoromethyl-substituted 2-phenylpyridine and tetraphenylimidodiphosphinate ligands
Lu, Guang-Zhao,Han, Hua-Bo,Li, Yan,Zheng, You-Xuan
, p. 33 - 41 (2017/04/24)
Four cyclometalated platinum complexes with trifluoromethyl-substituted 2-phenylpyridine at different positions on its phenyl group as the main ligands and tetraphenylimidodiphosphinate as the ancillary ligand, Pt1-Pt4 (Pt1 is a trifluoromethyl-free compl
