Mechanistic Studies of the Palladium-Catalyzed Amination of Aryl Halides and the Oxidative Addition of Aryl Bromides to Pd(BINAP)2and Pd(DPPF)2:  An Unusual Case of Zero-Order Kinetic Behavior and Product Inhibition

2000 ◽  
Vol 122 (19) ◽  
pp. 4618-4630 ◽  
Author(s):  
Luis M. Alcazar-Roman ◽  
John F. Hartwig ◽  
Arnold L. Rheingold ◽  
Louise M. Liable-Sands ◽  
Ilia A. Guzei
Keyword(s):  
Unusual Case ◽  
Oxidative Addition ◽  
Product Inhibition ◽  
Zero Order ◽  
Aryl Halides ◽  
Order Kinetic ◽  
Kinetic Behavior ◽  
Mechanistic Studies ◽  
Aryl Bromides ◽  
Palladium Catalyzed

scholarly journals Oxidative Addition of Aryl Halides to a Ni(I)-Bipyridine Complex

2022 ◽  
Author(s):  
Stephen Ting ◽  
Wendy Williams ◽  
Abigail Doyle
Keyword(s):  
Oxidative Addition ◽  
Aryl Halides ◽  
Solution Phase ◽  
Nickel Catalysis ◽  
Mechanistic Studies ◽  
Redox Equilibrium ◽  
Aryl Bromides ◽  
First Time

The oxidative addition of aryl halides to bipyridine- or phenanthroline-ligated nickel(I) is a commonly proposed step in nickel catalysis. However, there is a scarcity of complexes of this type that both are well-defined and undergo oxidative addition with aryl halides, hampering organometallic studies of this process. We report the synthesis of a well-defined Ni(I) complex, [(CO2Etbpy)NiCl]4 (1). Its solution-phase speciation is characterized by a significant population of monomer and a redox equilibrium that can be perturbed by π-acceptors and σ-donors. 1 reacts readily with aryl bromides, and mechanistic studies are consistent with a mechanism proceeding through an initial Ni(I) → Ni(III) oxidative addition. Such a process was demonstrated stoichiometrically for the first time, affording a structurally characterized Ni(III) aryl complex.

scholarly journals Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts

2020 ◽  
Vol 142 (7) ◽  
pp. 3564-3576 ◽  
Author(s):  
Antoine de Gombert ◽  
Alasdair I. McKay ◽  
Christopher J. Davis ◽  
Katherine M. Wheelhouse ◽  
Michael C. Willis
Keyword(s):  
Cross Coupling ◽  
Mechanistic Studies ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Oxidative Addition of Aryl Halides to Transient Anionic à-Aryl–Palladium(0) Intermediates—Application to Palladium-Catalyzed Reductive Coupling of Aryl Halides

1996 ◽  
Vol 2 (8) ◽  
pp. 957-966 ◽  
Author(s):  
Christian Amatore ◽  
Emmanuelle Carré ◽  
Anny Jutand ◽  
Hideo Tanaka ◽  
Qinghua Ren ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Aryl Halides ◽  
Reductive Coupling ◽  
Palladium Catalyzed

ChemInform Abstract: PALLADIUM-CATALYZED DOUBLE CARBONYLATION OF ARYL HALIDES TO GIVE α-KETO AMIDES. MECHANISTIC STUDIES

1985 ◽  
Vol 16 (38) ◽  
Author(s):  
F. OZAWA ◽  
H. SOYAMA ◽  
H. YANAGIHARA ◽  
I. AOYAMA ◽  
H. TAKINO ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Mechanistic Studies ◽  
Palladium Catalyzed

Palladium-Catalyzed Direct C2-Arylation of Benzo[b]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2812-2816 ◽  
Author(s):  
Fumiki Ichioka ◽  
Yuhei Itai ◽  
Yuji Nishii ◽  
Masahiro Miura
Keyword(s):  
Reaction System ◽  
Phenyl Group ◽  
Coupling Reaction ◽  
Direct Coupling ◽  
Aryl Halides ◽  
Facile Synthesis ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Direct coupling reaction of benzo[b]thiophene and electron-rich aryl bromides was achieved under Pd2(dba)3/SPhos catalysis in the presence of NaOt-Bu. The reaction system was applied for the installation of 2-(methylthio)phenyl group onto thiophene-fused polyaromatic molecules, demonstrating facile synthesis of precursors for thienoacene derivatives.

Oxidation of Pd(II) with Disilane in a Palladium-Catalyzed Disilylation of Aryl Halides: A Theoretical View

2021 ◽  
Author(s):  
Jing Zhang ◽  
Shihan Liu ◽  
Tao Zhang ◽  
Tao Liu ◽  
Yu Lan
Keyword(s):  
Density Functional Theory ◽  
Dft Calculations ◽  
Density Functional ◽  
Dft Calculation ◽  
Aryl Halide ◽  
Oxidative Addition ◽  
Aryl Halides ◽  
Functional Theory ◽  
Theoretical View ◽  
Palladium Catalyzed

Density functional theory (DFT) calculation has been used to reveal the mechanism of Pd-catalyzed disilylation reaction of aryl halide. The DFT calculations indicate that the reaction starts with oxidative addition...

scholarly journals Overcoming Limitations in Dual Photoredox/Nickel catalyzed C–N Cross-Couplings due to Catalyst Deactivation

2019 ◽  
Author(s):  
Sebastian Gisbertz ◽  
Susanne Reischauer ◽  
Bartholomäus Pieber
Keyword(s):  
Carbon Nitride ◽  
Catalyst Deactivation ◽  
Aryl Halides ◽  
Attractive Alternative ◽  
Nickel Catalysis ◽  
Broad Absorption ◽  
Aryl Bromides ◽  
Nitride Semiconductor ◽  
Palladium Catalyzed ◽  
High Concentrations

Dual photoreodox/nickel catalyzed C–N cross-couplings are an attractive alternative to the palladium catalyzed Buchwald-Hartwig reaction, but are limited to aryl halides containing electron-withdrawing groups. We show that the formation of catalytically inactive nickel-black is responsible for this limitation. Deposition of nickel-black further deactivates heterogeneous photocatalysts restricting their recyclability. We demonstrate that catalyst deactivation can be avoided by the combination of nickel catalysis and a carbon nitride semiconductor. The broad absorption range of the organic, heterogeneous photocatalyst enables a wavelength dependent reactivity control to prevent nickel-black formation. A second approach is to run the reactions at high concentrations to increase the formation of nickel-amine complexes that reduce nickel-black formation. This allows reproducible, selective C–N cross-couplings of electron-rich aryl bromides.<br>

Palladium-catalyzed double carbonylation of aryl halides to give .alpha.-keto amides. Mechanistic studies

1985 ◽  
Vol 107 (11) ◽  
pp. 3235-3245 ◽  
Author(s):  
Fumiyuki Ozawa ◽  
Hidehiko Soyama ◽  
Hisayoshi Yanagihara ◽  
Issei Aoyama ◽  
Hiroaki Takino ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Mechanistic Studies ◽  
Palladium Catalyzed
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