Category: 3796-23-4

Fier, Patrick S.; Kim, Suhong; Cohen, Ryan D. published the artcile< A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines>, Synthetic Route of 3796-23-4, the main research area is Boc protected aminopyridine chemoselective regioselective preparation; pyridine tert butyl chloro dicyanopyrazinyl oxy carbamate amination.

The development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines such as I [R = H, 3-Br, 4-Ph, etc.] with exquisite site selectivity and chemoselectivity was reported. The novel reagent was prepared on 200g scale in a single step, reacted in title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Exptl. and in situ spectroscopic monitoring techniques provided detailed insights and unexpected findings for the unique reaction mechanism.

Journal of the American Chemical Society published new progress about Amination, regioselective (chemoselective). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Synthetic Route of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Vogt, David B.; Seath, Ciaran P.; Wang, Hengbin; Jui, Nathan T. published the artcile< Selective C-F Functionalization of Unactivated Trifluoromethylarenes>, Related Products of 3796-23-4, the main research area is difluoroalkylarene preparation; trifluoromethylarene alkene photocatalytic alkylation.

Fluorinated organic mols. are pervasive within the pharmaceutical and agrochem. industries due to the range of structural and physicochem. properties that fluorine imparts. Currently, the most abundant methods for the synthesis of the aryl-CF2 functionality have relied on the deoxyfluorination of ketones and aldehydes using expensive and poorly atom economical reagents. Here, we report a general method for the synthesis of aryl-CF2R and aryl-CF2H compounds through activation of the corresponding trifluoromethyl arene precursors. This strategy is enabled by an endergonic electron transfer event that provides access to arene radical anions that lie outside of the catalyst reduction potential. Fragmentation of these reactive intermediates delivers difluorobenzylic radicals that can be intercepted by abundant alkene feedstocks or a hydrogen atom to provide a diverse array of difluoalkylaroms.

Journal of the American Chemical Society published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Related Products of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Xue; Ling, Liang; Luo, Meiming; Zeng, Xiaoming published the artcile< Accessing Difluoromethylated and Trifluoromethylated cis-Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization>, Name: 3-(Trifluoromethyl)pyridine, the main research area is difluoromethyl cis cycloalkane saturated heterocycle diastereoselective preparation; arene heteroarene cycloalkyl amino carbene rhodium catalyst dearomative reduction; trifluoromethyl cis cycloalkane saturated heterocycle diastereoselective preparation; heteroarene arene cycloalkyl amino carbene rhodium catalyst dearomative reduction; N-heterocyclic carbenes; fluorine; hydrogenation; reduction; rhodium.

A straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates preferential addition of hydrogen to substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction was reported. This strategy enabled diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes such as I [R = 2-COMe, 4-pyrazolyl, 3-OTBS, etc.; R1 = CF2H, CF3] and saturated heterocycles, e.g. II, and even allowed formation of all-cis multi-trifluoromethylated cyclic products with a defined equatorial orientation of the di- and trifluoromethyl groups. Deuterium-labeling studies indicated that hydrogen preferentially attacked substitution sites of planar arenes, resulting in dearomatization, possibly with heterogeneous Rh as reactive species, followed by either reversible or irreversible hydrogen addition to nonsubstitution sites.

Angewandte Chemie, International Edition published new progress about Aromatic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Name: 3-(Trifluoromethyl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mkrtchyan, Satenik; Jakubczyk, Michal; Lanka, Suneel; Yar, Muhammad; Ayub, Khurshid; Shkoor, Mohanad; Pittelkow, Michael; Iaroshenko, Viktor O. published the artcile< Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases>, Recommanded Product: 3-(Trifluoromethyl)pyridine, the main research area is trifluoromethyl group nitro compound ytterbium catalyst mechanochem coupling transformation; amide preparation; methanimine preparation; indole preparation.

Two mild, solvent-free mechanochem. coupling transformations of CF3 group with nitro compounds into amides or Schiff bases employing Ytterbia as a catalyst were reported. This process proceeded via C-F bond activation, accompanied with utilization of Si-based reductants/oxygen scavengers – reductants of the nitro group. The scope and limitations of the disclosed methodologies were thoroughly studied. To the best of author knowledge, this work was the first example of mech. energy promoted transformation of the inert CF3 group into other functionalities.

Advanced Synthesis & Catalysis published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Recommanded Product: 3-(Trifluoromethyl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kim, Sangmin; Loose, Florian; Bezdek, Mate J.; Wang, Xiaoping; Chirik, Paul J. published the artcile< Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters>, Synthetic Route of 3796-23-4, the main research area is phenylpyridinyl benzoquinolinyl cyclometalated pentamethylcyclopentadienylrhodium hydride multinuclear preparation crystal structure; hydrogenation heteroarene rhodium precatalyst reductive multimetallic rhodium cluster; crystal mol structure pentamethylcyclopentadienylrhodium multimetallic cluster.

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochem. or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, x-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent) (N-heteroarenes). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Synthetic Route of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ham, Won Seok; Choi, Hoonchul; Zhang, Jianbo; Kim, Dongwook; Chang, Sukbok published the artcile< C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization>, Product Details of C6H4F3N, the main research area is aminopyrimidine preparation DFT; pyrimidine nucleophilic functionalization.

A synthetic platform for site-selective C-H functionalization that affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products I (R = azanyl, 5-(trifluoromethyl)-1,2,3,4-tetrahydropyridin-1-yl, methylaminyl, etc.; R1 = H, Ph) in situ. was described. Mechanism-based reagent design allowed for the C2-selective amination of pyrimidines II, opening the new scope of site-selective heteroaryl C-H functionalization. This method is compatible with a broad range of pyrimidines II with sensitive functional groups, and can access complex aminopyrimidines I in high selectivity.

Journal of the American Chemical Society published new progress about Density functional theory. 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Product Details of C6H4F3N.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ou, Wei; Zou, Ru; Han, Mengting; Yu, Lei; Su, Chenliang published the artcile< Tailorable carbazolyl cyanobenzene-based photocatalysts for visible light-induced reduction of aryl halides>, Computed Properties of 3796-23-4, the main research area is dehalogenation arylation photocatalyst carbazole.

Herein, a series of carbazolyl cyanobenzene (CCB)-based organic photocatalysts with a broad range of photoredox capabilities were designed and synthesized, allowing precise control of the photocatalytic reactivity for the controllable reduction of aryl halides via a metal-free process. The screened-out CCB (5CzBN), a metal-free, low-cost, scalable and sustainable photocatalyst with both strong oxidative and reductive ability, exhibits superior performance for both dehalogenation and C-C bond-forming arylation reactions.

Chinese Chemical Letters published new progress about Arylation. 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Computed Properties of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wang, Amu; Liu, Ya-Zhou; Shen, Zhongke; Qiao, Zeen; Ma, Xiaofeng published the artcile< Regioselective Synthesis of Pyrazolo[1,5-a]pyridine via TEMPO-Mediated [3 + 2] Annulation-Aromatization of N-Aminopyridines and α,β-Unsaturated Compounds>, Safety of 3-(Trifluoromethyl)pyridine, the main research area is pyridiniumamine trimethylbenzenesulfonate alkene TEMPO catalyst regioselective annulation aromatization; pyrazolopyridine preparation.

A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines from N-aminopyridines and α,β-unsaturated compounds were developed. The procedure offered multisubstituted pyrazolo[1,5-a]pyridines in good to excellent yield with high and predictable regioselectivity. The modification of marketed drugs including Loratadine, Abiraterone and Metochalcone, a one-pot three-step gram scale synthesis of key intermediate for the preparation of Selpercatinib were demonstrated. Mechanism studies showed that TEMPO served both as a Lewis acid and as an oxidant.

Organic Letters published new progress about [3+2] Cycloaddition reaction (regioselective). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Safety of 3-(Trifluoromethyl)pyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Obradors, Carla; List, Benjamin published the artcile< Azine Activation via Silylium Catalysis>, Synthetic Route of 3796-23-4, the main research area is heteroarene silyl ketene acetal silylium phosphoramidimidate catalyst regioselective addition; silyl alkyl heteroarene preparation oxidation; alkyl heteroarene preparation.

A direct, catalytic and selective functionalization of azines via silylium activation was described. The catalyst design enabled mild conditions and a remarkable functional group tolerance in a one-pot setup.

Journal of the American Chemical Society published new progress about Acetals, ketene, silyl Role: RCT (Reactant), RACT (Reactant or Reagent). 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Synthetic Route of 3796-23-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhao, Li-Xia; Peng, Jian-Feng; Liu, Feng-Yi; Zou, Yue-Li; Gao, Shuang; Fu, Ying; Ye, Fei published the artcile< Design, Synthesis, and Herbicidal Activity of Diphenyl Ether Derivatives Containing a Five-Membered Heterocycle>, Product Details of C6H4F3N, the main research area is herbicide phenoxypyridine heterocycle derivative preparation protoporphyrinogen oxidase inhibitor; PPO; cumulative analysis; diphenyl ether derivatives; field trial; greenhouse herbicidal activity; molecular docking.

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is an important target for discovering novel herbicides, and it causes bleaching symptoms by inhibiting the synthesis of chlorophyll and heme. In this study, the active fragments of several com. herbicides were joined by substructure splicing and bioisosterism, and a series of novel di-Ph ether derivatives containing five-membered heterocycles were synthesized. The greenhouse herbicidal activity and the PPO inhibitory activity in vitro were discussed in detail. The results showed that most compounds had good PPO inhibitory activity, and target compounds containing trifluoromethyl groups tended to have higher activity. Among them, compound (I) showed the best inhibitory activity, with a half-maximal inhibitory concentration (IC50) of 0.0468 μmol/L, which was approx. 3 times better than that of oxyfluorfen (IC50 = 0.150 μmol/L). In addition, mol. docking indicated that compound I formed obvious π-π stacking interactions and hydrogen bond interactions with PHE-392 and ARG-98, resp. Remarkably, compound I had good safety for corn, wheat, rice, and soybean, and the cumulative concentration in crops was lower than that of oxyfluorfen. Therefore, compound I can be used to develop potential lead compounds for novel PPO inhibitors.

Journal of Agricultural and Food Chemistry published new progress about Abutilon theophrasti. 3796-23-4 belongs to class pyridine-derivatives, and the molecular formula is C6H4F3N, Product Details of C6H4F3N.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem