scholarly journals Synthesis and Structure of (Nitronyl Nitroxide-2-ido)(tert-butyldiphenylphosphine)gold(I) and -(Di(tert-butyl)phenylphosphine)gold(I) Derivatives; Their Comparative Study in the Cross-Coupling Reaction

Crystals ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 770
Author(s):  
Igor Zayakin ◽  
Irina Bagryanskaya ◽  
Dmitri Stass ◽  
Maxim Kazantsev ◽  
Evgeny Tretyakov
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Oxidation Potential ◽  
Nitronyl Nitroxide ◽  
X Ray ◽  
Tert Butyl ◽  
Cross Coupling Reaction ◽  
Vis Spectroscopy ◽  
The Cross ◽  
Derivatives Of

We synthesized two new organogold derivatives of a nitronyl nitroxide (NN) with phosphine ligands, namely NN-Au-PtBuPh2 and NN-Au-PtBu2Ph. They were characterized by X-ray diffraction analysis, cyclic voltammetry, and ESR, IR, and UV/Vis spectroscopy. The X-ray structural analysis revealed a tendency of the NN moiety to form a large number of short intermolecular contacts. This phenomenon is related to the anionic nature of the paramagnetic group NN, as evidenced by a significantly lower oxidation potential in comparison with purely organic derivatives of NN radicals. The cross-coupling reaction of NN-Au-PPh3, NN-Au-PtBuPh2, or NN-Au-PtBu2Ph with an activated bromoarene, namely, p-BrC6H4NO2, was investigated. It was shown that regardless of the presence of the bulky tert-butyl substituent, all gold derivatives have similar activities in the cross-coupling reaction and give a cross-coupling product, NN-C6H4NO2, with comparable yields.

scholarly journals Synthesis and Study of Chemical, Thermal, Mesomorphic, and Optical Properties of Terphenyls Modified with Nitrile Groups

2017 ◽  
Vol 2017 ◽  
pp. 1-9 ◽  
Author(s):  
M. L. Mota González ◽  
A. Carrillo Castillo ◽  
R. C. Ambrosio Lázaro ◽  
J. Flores Méndez ◽  
Mario Moreno ◽  
...  
Keyword(s):  
Optical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Photoluminescence Properties ◽  
X Ray Diffraction ◽  
Scanning Calorimetry ◽  
X Ray ◽  
H Nmr ◽  
Cross Coupling Reaction ◽  
Vis Spectroscopy

We report the synthesis, characterization, and the thermotropic and photoluminescence properties of dialkoxyterphenyls with (T12-CN and T12-2CN) and without (T12) nitrile groups. These terphenyls were prepared through the Suzuki-Miyaura cross-coupling reaction using a palladium-based catalyst. The products obtained were analyzed as powders or after being drop-casted or spin-coated on glass. Nuclear Magnetic Resonance (1H NMR) and Fourier Transform Infrared (FTIR) spectroscopy techniques confirmed the structure and purity of the synthesized terphenyls. The mesomorphic behavior was studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD). T12 developed various mesophases, whereas T12-CN and T12-2CN displayed one single mesophase of low order over a wide temperature range. The films topology was studied by AFM and the optical properties were determined by ultraviolet-visible (UV-Vis) spectroscopy and spectrofluorometry. Higher roughness was found for the films prepared with the asymmetric terphenyl (T12-CN). The photoluminescence (PL) spectrum obtained for the asymmetric terphenyl (T12-CN) exhibited the expected characteristics with an emission band centered at 381 nm and an overtone around 760 nm.

scholarly journals Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

2018 ◽  
Vol 14 ◽  
pp. 2384-2393
Author(s):  
Piotr Pomarański ◽  
Piotr Roszkowski ◽  
Jan K Maurin ◽  
Armand Budzianowski ◽  
Zbigniew Czarnocki
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
X Ray ◽  
H Nmr ◽  
Important Group ◽  
Cross Coupling Reaction ◽  
Efficient Access ◽  
Phenylboronic Acids ◽  
Derivatives Of ◽  
Single Bonds

Background: Atropisomers are very interesting stereoisomers having axial chirality resulting from restricted rotation around single bonds and are found in various classes of compounds. ortho-Substituted arylpyridines are an important group of them. A regio- and atropselective Suzuki–Miyaura cross-coupling reaction on 3,4,5-tribromo-2,6-dimethylpyridine was studied. Results: Reactions with various amounts of ortho-substituted phenylboronic acids with 3,4,5-tribromo-2,6-dimethylpyridine gave a series of mono- di- and triarylpyridine derivatives which allowed to draw conclusions about the order of substitution. Also, the observed selectivity in the case of ortho-methoxyphenylboronic acid suggested an additional metal O-chelation effect in the transition state, apparently not present in the ortho-chloro analogues. The rotational barrier in selected atropisomers was determined on the basis of HT NMR and thermal epimerisation experiments. The structure of most presented atropisomeric derivatives of 2,6-dimethylpyridine was confirmed by single-crystal X-ray analysis. Racemic chiral, differently substituted atropisomers were also examined by 1H NMR spectroscopy in the presence of a chiral solvating agent. Conclusion: This regio- and atropselectivity may be generally applicable to other arylpyridine systems. A regio- and atropselective Suzuki–Miyaura cross-coupling process has been observed, giving an efficient access to a class of atropisomeric compounds. An opposite selectivity using a differently ortho-substituted phenylbornic acid was observed.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivative ◽  
Tert Butyl ◽  
Radical Coupling ◽  
Air Atmosphere ◽  
Cross Coupling Reaction ◽  
Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

Pd-catalyzed desulfitative arylation of olefins by N-methoxysulfonamide

2022 ◽  
Author(s):  
Subhadra Ojha ◽  
Niranjan Panda
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Type Reaction ◽  
Cross Coupling Reaction ◽  
The Cross

A novel Pd-catalyzed protocol desulfitative Heck type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtainaryl alkenes....

scholarly journals A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3612 ◽  
Author(s):  
Akhilesh Sharma ◽  
Masaharu Nakamura
Keyword(s):  
Density Functional ◽  
Molecular Mechanic ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dft Study ◽  
Reaction Pathways ◽  
Hydrogen Elimination ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
A Chain

To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others.

scholarly journals Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 652 ◽  
Author(s):  
Monika Olesiejuk ◽  
Agnieszka Kudelko ◽  
Marcin Swiatkowski ◽  
Rafal Kruszynski
Keyword(s):  
Ionic Liquids ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Luminescence Properties ◽  
Coupling Reactions ◽  
Triazole Derivatives ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Derivatives Of

New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

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