Day: January 5, 2023

Directed Aromatic C-H Activation/Acetoxylation Catalyzed by Pd Nanoparticles Supported on Graphene Oxide was written by Zhang, Yi;Zhao, Yu;Luo, Yu;Xiao, Liuqing;Huang, Yuxing;Li, Xingrong;Peng, Qitao;Liu, Yizhen;Yang, Bo;Zhu, Caizhen;Zhou, Xuechang;Zhang, Junmin. And the article was included in Organic Letters in 2017.Formula: C12H11N This article mentions the following:

The first solid-supported directed aromatic C-H activation/acetoxylation has been successfully developed by using palladium nanoparticles supported on graphene oxide (PdNPs/GO) as a catalyst. The practicability of this method is demonstrated by simple preparation of catalyst, high catalytic efficiency, wide functional group tolerance, and easy scale up of the reaction. A hot filtration test and Hg(0) poisoning test indicate the heterogeneous nature of the catalytic active species. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Formula: C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of Phenanthridines via a Rhodium-Catalyzed C-C Bond Cleavage Reaction of Biphenylene with Nitriles was written by Korotvicka, Ales;Frejka, David;Hampejsova, Zuzana;Cisarova, Ivana;Kotora, Martin. And the article was included in Synthesis in 2016.Recommanded Product: 6-Fluoropicolinonitrile This article mentions the following:

The reaction of biphenylene with various nitriles in the presence of catalytic amount of bis[(1,2,5,6-η)-1,5-cyclooctadiene]rhodium(1+) tetrafluoroborate(1-) [i.e., [Rh(cod)₂BF₄]] and dppe under microwave irradiation afforded 9-substituted phenanthridines. The reaction with alkyl and aromatic nitriles provided the corresponding 9-substituted phenanthridines in 26-79% isolated yields. The reaction was also carried out with cyanopyridines and it provided heterocyclic compounds with the bipyridine and terpyridine scaffold. The synthesized bipyridine and terpyridine were complexed with [Rh(cod)Cl]₂. The former provided a Rh(III) complex in which the cyclooctadiene moiety was oxidized to the THF ring, whereas the latter gave a structurally fluxional complex (in solution) with only one pyridine ring coordinated to the rhodium atom. The title compounds thus formed included 6-(3-chlorophenyl)phenanthridine, 3-(6-phenanthridinyl)benzonitrile, 6-(2-thienyl)phenanthridine (thiophene), 6-(2-furanyl)phenanthridine (furan), 6-(2-pyridinyl)phenanthridine. The synthesis of the target compound was achieved by a reaction of 6-(2-pyridinyl)phenanthridine (i.e., a bipyridine analog) with di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium [i.e., [Rh(COD)Cl]₂ cyclooctadiene-group oxidation]. The title compound thus formed was a 9-Oxabicyclo[4.2.1]nonane-(pyridinyl)phenanthridine-rhodium complex. In the experiment, the researchers used many compounds, for example, 6-Fluoropicolinonitrile (cas: 3939-15-9Recommanded Product: 6-Fluoropicolinonitrile).

6-Fluoropicolinonitrile (cas: 3939-15-9) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Recommanded Product: 6-Fluoropicolinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Etherification of Functionalized Phenols with Chloroheteroarenes at Low Palladium Loading: Theoretical Assessment of the Role of Triphosphane Ligands in C-O Reductive Elimination was written by Platon, Melanie;Cui, Luchao;Mom, Sophal;Richard, Philippe;Saeys, Mark;Hierso, Jean-Cyrille. And the article was included in Advanced Synthesis & Catalysis in 2011.Electric Literature of C11H9NO This article mentions the following:

The present study highlights the potential of robust tridentate ferrocenylphosphanes with controlled conformation as catalytic auxiliaries in C-O bond formation reactions. Air-stable Pd triphosphane systems are efficient for selective heteroaryl ether synthesis by using ≥0.2 mol% of catalyst. These findings represent an economically attractive and clean etherification of functionalized phenols, electron-rich, electron-poor and para-, meta- or ortho-substituted substrates, with heteroaryl chlorides, including pyridines, hydroxylated pyridine, pyrimidines and thiazole. The etherification tolerates very important functions in various positions, such as cyano, methoxy, amino, and fluoro groups, which is useful to synthesize bioactive mols. DFT studies also demonstrate that triphosphane ligands open up various new pathways for the C-O reductive elimination involving the 3rd phosphane group. In particular, the rate for one of these new pathways is ∼1000 times faster than for reductive elimination from a complex with a similar ferrocenyl ligand, but without a phosphane group on the bottom Cp-ring. Coordination of the 3rd phosphane group to the Pd(II) center is calculated to stabilize the transition state in this new pathway, thereby enhancing the reductive elimination rate. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Electric Literature of C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Electric Literature of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rhodium(III)-catalyzed chelation-assisted C-H imidation of arenes via umpolung of the imidating reagent was written by Zheng, Guangfan;Sun, Jiaqiong;Xu, Youwei;Zhou, Xukai;Gao, Hui;Li, Xingwei. And the article was included in Chinese Journal of Catalysis in 2020.SDS of cas: 4373-61-9 This article mentions the following:

Rh(III)-catalyzed, chelation-assisted oxidative C-H imidation of arenes with N-H imide was realized using PhI(OAc)₂ as an oxidant. This transformation exhibits a broad substrate scope and tolerates various functional groups. The reaction proceeded via in-situ generation of an iodine(III) imido. DFT calculations suggest that this oxidative imidation system proceeds via a Rh(III)-Rh(V)-Rh(III) pathway. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9SDS of cas: 4373-61-9).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.SDS of cas: 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bis(2,2,2-trifluoroethyl)(2-cyanoethyl) phosphate – a new uranium extragent was written by Nalibayeva, A. M.;Bishimbayeva, G. K.;Saidullayeva, S. A.;Verhoturova, S. I.;Arbuzova, S. N.;Gusarova, N. K.. And the article was included in Izvestiya Natsional’noi Akademii Nauk Respubliki Kazakhstan, Seriya Khimii i Tekhnologii in 2020.Application of 628-13-7 This article mentions the following:

Organophosphate compounds are widely used in industrial hydrometallurgical processes as extractants and complexones of non-ferrous, noble, rare-earth metals and transuranic elements. Among these compounds, organic phosphates occupy a special place, as they allow for the extraction processes with good selectivity and efficiency. Therefore, the search and development of new uranium effective extractants is an important task for the development of modern hydrometallurgical processes. For this functional phosphate containing a cyano group, one should expect a synergistic effect of the extraction properties of the phosphates themselves, as well as of the known extractants – contribute to an increase in its incombustibility. Thus, the use of this extractant in the production of the extraction of uranium from uranium-containing nitric acid or sulfuric acid solutions was 20.7% and 18.7%; the content of uranium in the extractant was 63.9 g/dm3 and 49. 7 g/dm3, resp. Pos. results were also obtained when studying the synergistic properties of the new extractant and the traditional – bis(2-ethylhexyl) phosphate. Using a mixture of these extractants (their weight ratio was 1:1.2) allows you to extract 57% of uranium from the uranium sulfate solution The use of bis(2,2,2-trifluoroethyl)(2-cyanoethyl) phosphate as a new extractant makes it possible to extract up to 20.7% of uranium from technol. nitrate or sulfate of uranium-containing solutions In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Application of 628-13-7).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Application of 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ion pairing in 1-butyl-3-methylpyridinium halide ionic liquids studied using NMR and DFT calculations was written by Swamy, Vincent P.;Thulasiram, Hirekodathakallu V.;Rastrelli, Federico;Saielli, Giacomo. And the article was included in Physical Chemistry Chemical Physics in 2018.Synthetic Route of C10H16ClN This article mentions the following:

We present the ¹H, ¹³C and ¹⁵N NMR chem. shifts of bulk ionic liquids based on 1-butyl-3-methylimidazolium (the cation also known as 1-butyl-3-picolinium) halides (Cl^–, Br^– and I^–) and tribromide (Br₃^–) salts. A characterization in solution of the analogous ICl₂^– and I₃^– salts is also reported. A series of DFT calculations has been run to predict the features of the NMR spectra of the pure ILs based on a few selected supramol. ionic aggregates. To test the effect of temperature, and vibrational and conformational motions, only for the chloride salt, we also run first-principles mol. dynamics simulations of the ion pair in the gas phase, using the ADMP scheme (Atom Centered D. Matrix Propagation mol. dynamics model). The aim of our investigation is to test whether a simple DFT based approach of ion-pairing in ionic liquids is capable of providing reliable results and under which conditions the protocol is robust. We obtained a very good agreement between the calculated and exptl. spectra for the three halides, where the bulk structure of the ILs is dominated by H-bond interactions between the X^– anion (X = Cl, Br and I) and the ortho protons of the pyridinium ring (a structural arrangement not too different from the solid-state structure of pyridinium halides). In contrast, when the H-bond is weak, as in the Br₃^– case, a number of supramol. arrangements exist in solution and the simple DFT calculations of a few selected cases cannot exhaustively explore the complete energy landscape. Moreover, the dynamic effects due to thermal motion, evaluated by ADMP MD simulations of the chloride salt, appear to be not very significant. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Synthetic Route of C10H16ClN).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Synthetic Route of C10H16ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Crystallization and Glass-Forming Ability of Ionic Liquids: Novel Insights into Their Thermal Behavior was written by Lobo Ferreira, Ana I. M. C.;Rodrigues, Ana S. M. C.;Villas, Miguel;Tojo, Emilia;Rebelo, Luis Paulo N.;Santos, Luis M. N. B. F.. And the article was included in ACS Sustainable Chemistry & Engineering in 2019.Electric Literature of C11H17N This article mentions the following:

This work presents an extended study of the thermal behavior of the alkyl and dialkylpyridinium derivatives of the bis(trifluoromethylsulfonyl)imide ionic liquid series, using high resolution power compensation differential scanning calorimetry (DSC) equipment. Temperatures, enthalpies, entropies, and the heat capacity change associated with the glass transition, as well as cold crystallization, solid-solid transitions, and melting, are used to evaluate their ability to form a glass and crystallize. The effects of the cation isomerization and the alkyl chain length increase were used to investigate the nature of the irregular thermal behavior of ionic liquids in general and to establish the link between their thermal properties and nanostructuration. The observed V-shape profile of the melting temperatures vs. the alkyl side-chain length is interpreted as a consequence of the balance between the initial decrease of the magnitude of the electrostatic interaction and the regular increase of the dispersive van der Waals forces. The observed differentiation between the thermal behavior below and above the critical alkyl size, CAS, is analyzed and compared with the regular behavior of both the n-alkanes and the n-alkanols. Above the CAS, the entropy and enthalpy profiles present trends similar to those observed in the alkane and alc. series, contrasting with those observed in the molten salts-like region. These results and evidence are a strong support to the interpretation of the effect of the ILs nanostructuration in the phys.-chem. properties. We found a great similarity between the thermal behavior of the imidazolium and pyridinium cation core, highlighting the strong ability of ILs to form a nanostructured network with distinguishable polar and nonpolar domains in the liquid phase. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Electric Literature of C11H17N).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Electric Literature of C11H17N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Experimental and theoretical studies on rhodium-catalyzed direct C-H benzoxylation reaction was written by Jin, Chen;Wang, Guimin;Yang, Xueyan;Zhu, Weiliang;Yang, Yaxi. And the article was included in Tetrahedron Letters in 2018.Related Products of 4373-61-9 This article mentions the following:

The green and efficient rhodium-catalyzed, chelation assisted C-H benzoxylation reaction of electron donating group containing benzenes with hydroxy-benziodoxolone was developed to yield mono-oxidation i.e. I [R = H, 3-Me, 4-OMe, etc.; R¹ = 2-pyridyl, 2-pyrimidinyl, 1-pyrazolyl; R² = OC(O)-2-I-C₆H₄] and di-oxidation i.e. II products which released water as the single byproduct. The reaction proceeded under mild conditions with controllable mono- and dioxygenation selectivity. DFT calculations supported the nucleophilic addition pathway was most likely involved in the current reaction system. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Related Products of 4373-61-9).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Related Products of 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Dual Emission, Aggregation, and Redox Properties of Boron Difluoride Hydrazones Functionalized with Triphenylamines was written by Cappello, Daniela;Buguis, Francis L.;Boyle, Paul D.;Gilroy, Joe B.. And the article was included in ChemPhotoChem in 2022.Application of 91-02-1 This article mentions the following:

π-Conjugated mol. materials often exhibit interesting photoluminescence, redox, and optoelectronic properties that grant them utility as light-harvesting materials in solar cells, as the emissive component of organic light-emitting diodes, and as fluorescence sensors. Preparing dye conjugates by appending multiple dyes together to generate π-conjugated mols. is a common strategy to enhance the properties of these materials as it often imparts traits that cannot be achieved by the building blocks independently. Herein, we report mol. materials that incorporate boron difluoride hydrazone (BODIHY) and triphenylamine (TPA) units that exhibit charge-transfer character, dual-emission, and aggregation-induced emission. The title compounds have low-energy absorption bands (λ_abs=455-493 nm) that are red-shifted relative to BODIHYs with smaller π-systems and exhibit dual-emission in the solution, solid, and aggregate states. TPA-BODIHY (donor-acceptor) conjugates show multiple reversible redox events and, in combination, the data presented herein indicate that there is electronic communication throughout the donor-acceptor and acceptor-donor-acceptor π-systems. These results are rationalized with the use of computational chem. and solid-state structural anal. This study provides new opportunities for the design of mol. materials that are comprised of redox-active photoluminescent dyes, including BODIHY, and their potential applications. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Application of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A comparative study of certain sulfisoxazole synthetic methods was written by Oeriu, S.;Voinescu, M.;Lupu, E.;Gloter, E.. And the article was included in Studii si Cercetari de Chimie in 1957.Synthetic Route of C12H8N4O This article mentions the following:

The 3 methods indicated (loc. cit.) for the synthesis of α-acetylpropionitrile, which on cyclization yielded dimethylaminoisoxazole were compared as were also the diverse variations for coupling the amine with p-acetamidobenzenesulfonyl chloride, and hydrolyzing the product. (11 references). In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Synthetic Route of C12H8N4O).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Synthetic Route of C12H8N4O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem