Organolanthanide and organoactinide oxidative additions exhibiting enhanced reactivity. 5. Stoichiometry, kinetic and mechanistic studies of (C5Me5)2YbII.cntdot.OEt2 oxidative-addition reactions and of (C5Me5)2YbIIIR "YbIII-Grignard" reactions with alkyl and aryl halides. Evidence for the dominance of inner-sphere mechanisms

1989 ◽  
Vol 8 (2) ◽  
pp. 263-277 ◽  
Author(s):  
R. G. Finke ◽  
S. R. Keenan ◽  
P. L. Watson
Keyword(s):  
Oxidative Addition ◽  
Aryl Halides ◽  
Addition Reactions ◽  
Mechanistic Studies ◽  
Oxidative Additions ◽  
Grignard Reactions ◽  
Inner Sphere

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 Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

2021 ◽  
Author(s):  
Ryota Isshiki ◽  
Miki B. Kurosawa ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Exchange Reaction ◽  
Ligand Exchange ◽  
Aryl Halides ◽  
Mechanistic Studies ◽  
Aromatic Esters ◽  
Oxidative Additions ◽  
Aryl Sulfides ◽  
Aryl Sulfide

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl–S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl–Ni–SR and aryl–Ni–OAr species to furnish aryl exchanged compounds.

Dinuclear oxidative addition reactions using an isostructural series of Ni2, Co2, and Fe2 complexes

2017 ◽  
Vol 46 (17) ◽  
pp. 5493-5497 ◽  
Author(s):  
Michael J. Behlen ◽  
You-Yun Zhou ◽  
Talia J. Steiman ◽  
Sudipta Pal ◽  
Douglas R. Hartline ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Addition Reactions ◽  
Oxidative Additions ◽  
Redox Active ◽  
Metal Metal ◽  
Metal Metal Bonds ◽  
Metal Bonds

Dinuclear oxidative additions at metal–metal bonds are facilitated by redox-active supporting ligands.

scholarly journals Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

2021 ◽  
Author(s):  
Ryota Isshiki ◽  
Miki B. Kurosawa ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Exchange Reaction ◽  
Ligand Exchange ◽  
Aryl Halides ◽  
Mechanistic Studies ◽  
Aromatic Esters ◽  
Oxidative Additions ◽  
Aryl Sulfides ◽  
Aryl Sulfide

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl–S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl–Ni–SR and aryl–Ni–OAr species to furnish aryl exchanged compounds.

Oxidative addition reactions of aryl halides on [NiBr(PPh3)3]

1984 ◽  
Vol 267 (2) ◽  
pp. 213-219 ◽  
Author(s):  
M. Anton ◽  
N. Clos ◽  
G. Müller
Keyword(s):  
Oxidative Addition ◽  
Aryl Halides ◽  
Addition Reactions
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