Organic chemistry of subvalent transition complexes. 9. Oxidative addition of nickel(0) complexes to carbon-carbon bonds in biphenylene: formation of nickelole and 1,2-dinickelecin intermediates

1985 ◽  
Vol 4 (2) ◽  
pp. 224-231 ◽  
Author(s):  
John J. Eisch ◽  
Andrzej M. Piotrowski ◽  
Kyoung I. Han ◽  
Carl. Kruger ◽  
Y. H. Tsay
Keyword(s):  
Organic Chemistry ◽  
Oxidative Addition ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Transition Complexes

Die oxidative Addition von NickeI(0)-KompIexen an Kohlenstoff-Kohlenstoff-Bindungen im Cyclobutadien. Zur Frage der Überführbarkeit von Cyclobutadien-Nickel(O)-Komplexen in Nickelaringe / Oxidative Addition of Nickel(O) Complexes to Carbon-Carbon Bonds in Cyclobutadiene. The Question of the Interconvertibility of Cyclobutadiene-nickel(O) Complexes and the Nickelaring Systems

1985 ◽  
Vol 40 (5) ◽  
pp. 624-635 ◽  
Author(s):  
John J. Eisch ◽  
Andrzej M. Piotrowski ◽  
Allen A. Aradi ◽  
Carl Krüger ◽  
Maria J. Romão
Keyword(s):  
Spectral Data ◽  
Structure Determination ◽  
Oxidative Addition ◽  
Subsequent Treatment ◽  
X Ray ◽  
X Ray Crystallography ◽  
Carbon Carbon Bonds ◽  
Elemental Analyses ◽  
Carbon Bonds

Abstract Bis(triethylphosphine)(η4-tetraphenylcyclobutadiene)nickel (4) was synthesized by the reduction of (η4-tetraphenylcyclobutadiene)nickel(II)bromide (3) with t-butyllithium in the presence of Et3P, and its structure was determined by X-ray crystallography. Furthermore, its reactivity towards CO, CH3CO2H, PhC≡CPh, LiAlH4 and O2 were investigated. 1,1-Bis(triethylphos-phine)-2,3,4,5-tetraphenylnickelole (14) was synthesized from (E,E)-1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene (15) and bis(triethylphosphine)nickel(II)bromide. Since the resulting crystals of the nickelole were not suitable for X-ray structure determination, the compound was characterized by elemental analyses, spectral data and carbonylation to yield tetraphenylcyclo-pentadienone (6).Analogous reductions of (η4 -tetraphenylcyclobutadiene)nickel(II)bromide (3) in the presence of Ph3P or Ph2PCH2CH2PPh2 , followed by carbonylation, led to 6 in 40% yield, demonstrating that about half of the cyclobutadiene rings in 3 undergo cleavage upon reduction to give the nickelole.Reactions of the dilithium reagent 15 with NiBr2 complexed with Me2PCH2CH2PMe2 ,Ph3P or Et2PCH2CH2PEt2 , led to the formation of thermolabile nickeloles, as demonstrated by carbonylàtion which yielded 6. Warming of the nickeloles and subsequent treatment with CH3CO2H led to the formation of 1,2,3,4,5,6,7,8-octaphenyl-1,3,5,7-octatetraene (8) and, in one case, octaphenyl-cyclooctatetraene (5).The relevance of these findings to the mechanism of the Reppe nickel-catalyzed oligomerization of alkynes is discussed.

Applications of Photoredox Catalysis for the Radical-Induced Cleavage of C-C Bonds

Synthesis ◽  
2021 ◽  
Author(s):  
Shoubhik Das ◽  
Jaro Vanderghinste
Keyword(s):  
Organic Chemistry ◽  
Relative Strength ◽  
Photoredox Catalysis ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

Selective cleavage of C-C bonds forms one of the greatest challenges in current organic chemistry, due to the relative strength of these bonds. However, such transformations are an invaluable instrument to break down and construct new carbon-carbon bonds. To achieve this, photochemistry can be used as a valuable tool to generate radicals and induce the cleavage of these bonds. This review paints a picture of some of the most influential contributions in this field from the last decade.

Oxidative Addition of Carbon-Carbon Bonds to Gold

2015 ◽  
Vol 127 (17) ◽  
pp. 5325-5329 ◽  
Author(s):  
Maximilian Joost ◽  
Laura Estévez ◽  
Karinne Miqueu ◽  
Abderrahmane Amgoune ◽  
Didier Bourissou
Keyword(s):  
Oxidative Addition ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

scholarly journals Oxidative Addition of Carbon–Carbon Bonds with a Redox-Active Bis(imino)pyridine Iron Complex

2012 ◽  
Vol 134 (41) ◽  
pp. 17125-17137 ◽  
Author(s):  
Jonathan M. Darmon ◽  
S. Chantal E. Stieber ◽  
Kevin T. Sylvester ◽  
Ignacio Fernández ◽  
Emil Lobkovsky ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Iron Complex ◽  
Redox Active ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

Oxidative Addition of Carbon-Carbon Bonds to Gold

2015 ◽  
Vol 54 (17) ◽  
pp. 5236-5240 ◽  
Author(s):  
Maximilian Joost ◽  
Laura Estévez ◽  
Karinne Miqueu ◽  
Abderrahmane Amgoune ◽  
Didier Bourissou
Keyword(s):  
Oxidative Addition ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds
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