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

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.

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

scholarly journals Broad scope gold(i)-catalysed polyenyne cyclisations for the formation of up to four carbon–carbon bonds

2017 ◽  
Vol 15 (10) ◽  
pp. 2163-2167 ◽  
Author(s):  
Zhouting Rong ◽  
Antonio M. Echavarren
Keyword(s):  
Single Step ◽  
Simultaneous Formation ◽  
Broad Scope ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
First Time ◽  
High Stereoselectivity

The polycyclisation of polyeneynes catalyzed by gold(i) has been extended for the first time to the simultaneous formation of up to four carbon–carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings.

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