Mechanism, Reactivity, and Selectivity in Palladium-Catalyzed Organosilicon-Based Cross Coupling Reaction

2021 ◽  
Author(s):  
Qian Wang ◽  
Hui-Mei Jiang ◽  
Shuping Zhuo ◽  
Li-Ping Xu
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dft Study ◽  
Functional Theory ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Strain Release

A comprehensive density functional theory (DFT) study has been performed to elucidate the mechanistic details of the Pd-catalyzed strain-release organosilicon based cross coupling reaction of four- and five-membered silacycles. The...

scholarly journals A novel selective fluorescent chemosensor for Fe3+ ions based on phthalonitrile dimer: synthesis, analysis, and theoretical studies

2020 ◽  
Vol 44 (5) ◽  
pp. 1254-1264
Author(s):  
Shaya AL-RAQA ◽  
İpek ÖMEROĞLU ◽  
Doğan ERBAHAR ◽  
Mahmut DURMUŞ
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Interaction Mechanism ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Density Functional Theory Calculations ◽  
Theoretical Studies ◽  
Functional Theory ◽  
Cross Coupling Reaction ◽  
Ft Ir

Phenyl-4,4-di(3,6-dibutoxyphthalonitrile) (3) was synthesized by the reaction of 1,4-phenylenebisboronic acid (1) and 4-bromo-3,6-dibutoxyphthalonitrile (2), using Suzuki cross-coupling reaction. The newly synthesized compound (3) was characterized by FT-IR, MALDI-MS, ESI-MS, 1H-NMR, 13C-NMR, and 13C-DEPT-135-NMR. The fluorescence property of phenyl-4,4-di(3,6- dibutoxyphthalonitrile) (3) towards various metal ions was investigated by fluorescence spectroscopy, and it was observed thatthe compound (3) displayed a significantly ‘turn-off’ response to Fe3+, which was referred to 1:2 complex formation between ligand (3) and Fe3+. The compound was also studied via density functional theory calculations revealing the interaction mechanism of the molecule with Fe3+ ions.

Density Functional Theory Investigation of the Alkyl-Alkyl Negishi Cross-Coupling Reaction Catalyzed by N-Heterocyclic Carbene (NHC)-Pd Complexes

2009 ◽  
Vol 15 (17) ◽  
pp. 4281-4288 ◽  
Author(s):  
Gregory A. Chass ◽  
Christopher J. O'Brien ◽  
Niloufar Hadei ◽  
Eric Assen B. Kantchev ◽  
Wei-Hua Mu ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Functional Theory ◽  
Cross Coupling Reaction ◽  
Pd Complexes

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.

The Palladium-Catalyzed Cross-Coupling Reaction of Carboxylic Anhydrides with Arylboronic Acids:  A DFT Study

2005 ◽  
Vol 127 (31) ◽  
pp. 11102-11114 ◽  
Author(s):  
Lukas J. Goossen ◽  
Debasis Koley ◽  
Holger L. Hermann ◽  
Walter Thiel
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Dft Study ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Mechanistic insight into the selective cyclization of arylnitrones to indolines via Rh(iii) catalyst: a theoretical study

RSC Advances ◽  
2016 ◽  
Vol 6 (28) ◽  
pp. 23265-23271 ◽  
Author(s):  
Tao Liu ◽  
Xiao-Wen Zheng ◽  
Ling-Li Han ◽  
Ya-Ping Li ◽  
Shu-Min Han ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Theoretical Study ◽  
Coupling Reaction ◽  
Dft Study ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Mechanistic Insight ◽  
Insight Into

A density functional theory (DFT) study was performed to understand detailed mechanisms for the Rh(iii)-catalyzed coupling reaction of phenylnitrone with diphenylacetylene in different reaction conditions.

scholarly journals Synthesis of Pyridazine Derivatives by Suzuki-Miyaura Cross-Coupling Reaction and Evaluation of Their Optical and Electronic Properties through Experimental and Theoretical Studies

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3014 ◽  
Author(s):  
Sara Fernandes ◽  
João Aires-de-Sousa ◽  
Michael Belsley ◽  
M. Raposo
Keyword(s):  
Density Functional ◽  
Rayleigh Scattering ◽  
Second Harmonic ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Fundamental Wavelength ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Dipolar Moment ◽  
Pyridazine Derivatives

A series of π-conjugated molecules, based on pyridazine and thiophene heterocycles 3a–e, were synthesized using commercially, or readily available, coupling components, through a palladium catalyzed Suzuki-Miyaura cross-coupling reaction. The electron-deficient pyridazine heterocycle was functionalized by a thiophene electron-rich heterocycle at position six, and different (hetero)aromatic moieties (phenyl, thienyl, furanyl) were functionalized with electron acceptor groups at position three. Density Functional Theory (DFT) calculations were carried out to obtain information on the conformation, electronic structure, electron distribution, dipolar moment, and molecular nonlinear response of the synthesized push-pull pyridazine derivatives. Hyper-Rayleigh scattering in 1,4-dioxane solutions, using a fundamental wavelength of 1064 nm, was used to evaluate their second-order nonlinear optical properties. The thienylpyridazine functionalized with the cyano-phenyl moiety exhibited the largest first hyperpolarizability (β = 175 × 10−30 esu, using the T convention) indicating its potential as a second harmonic generation (SHG) chromophore.

scholarly journals Synthesis of 3,4-Biaryl-2,5-Dichlorothiophene through Suzuki Cross-Coupling and Theoretical Exploration of Their Potential Applications as Nonlinear Optical Materials

Symmetry ◽  
2018 ◽  
Vol 10 (12) ◽  
pp. 766
Author(s):  
Nasir Mahmood ◽  
Nasir Rasool ◽  
Hafiz Ikram ◽  
Muhammad Hashmi ◽  
Tariq Mahmood ◽  
...  
Keyword(s):  
Density Functional ◽  
Minimum Energy ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Energy Structure ◽  
One Pot ◽  
Structure And Property ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Nlo Materials

We report herein the efficient one-pot synthesis of 3,4-biaryl-2,5-dichlorothiophene derivatives (2a–2i) via a palladium-catalyzed Suzuki cross-coupling reaction. A series of thiophene derivatives were synthesized, starting from 3,4-dibromo-2,5-dichlorothiophene (1) and various arylboronic acids using Pd(PPh3)4 and K3PO4 with moderate to good yields. For further insights about the structure and property relationship, density functional theory (DFT) calculations were performed. A relaxed potential energy surface (PES) scan was performed to locate the minimum energy structure. A frontier molecular orbitals analysis was performed to explain the reactivity of all synthesized derivatives. As the synthesized derivatives had extended conjugations, therefore the first hyperpolarizability (βo) was calculated to investigate their potential as non-linear optical (NLO) materials and significant βo values were found for the 2b and 2g derivatives.

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>

scholarly journals Boron and nitrogen doping in graphene: an experimental and density functional theory (DFT) study

Nano Express ◽  
2020 ◽  
Vol 1 (1) ◽  
pp. 010027
Author(s):  
Cantekin Kaykılarlı ◽  
Deniz Uzunsoy ◽  
Ebru Devrim Şam Parmak ◽  
Mehmet Ferdi Fellah ◽  
Özgen Çolak Çakır
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Nitrogen Doping ◽  
Dft Study ◽  
Functional Theory
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