244988
Bis(1,5-cyclooctadiene)nickel(0)
Synonym(s):
Bis(cyclooctadiene)nickel, Ni(COD)2
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About This Item
Empirical Formula (Hill Notation):
C16H24Ni
CAS Number:
Molecular Weight:
275.06
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
215-072-0
MDL number:
Quality Level
reaction suitability
core: nickel, reaction type: Cross Couplings, reagent type: catalyst
parameter
temperature sensitive
mp
60 °C (dec.) (lit.)
storage temp.
−20°C
SMILES string
[Ni].C1CC=CCCC=C1.C2CC=CCCC=C2
InChI
1S/2C8H12.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H,3-6H2;/b2*2-1-,8-7-;
InChI key
JRTIUDXYIUKIIE-KZUMESAESA-N
Application
Reactant for:
Catalyst for:
- Oxidative addition reactions
Catalyst for:
- Asymmetric α-arylation and heteroarylation of ketones with chloroarenes
- Cross-coupling reactions
- Regioselective and stereoselective carboxylation/cyclization of allenyl aldehydes under a carbon dioxide atmosphere
- Methyl carboxylation of homopropargylic alcohols
- Stereoselective borylative ketone-diene coupling
- Cycloaddition of benzamides with internal alkynes
Used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. The reaction with terminal acetylenes proceeds in high yield and high selectivity. A variety of functional groups are tolerated.
Catalyst for the cycloaddition of 1,3-dienes.
signalword
Danger
hcodes
Hazard Classifications
Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1
target_organs
Lungs
Storage Class
4.1B - Flammable solid hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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G Eliad Benitez-Medina et al.
Dalton transactions (Cambridge, England : 2003), 48(47), 17579-17587 (2019-11-22)
The nickel-catalyzed N-alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the C[double bond, length as m-dash]N
Tiziana Funaioli et al.
PloS one, 5(5), e10617-e10617 (2010-05-21)
It is well known that, stemming from the mutual interplay between chromophores, circular dichroism (CD) is a powerful technique to deal with structural problems for both the small organic molecule and the biopolymer. However, quantitative interpretations of the spectroscopic and
Quanyou Feng et al.
Nature communications, 9(1), 1559-1559 (2018-04-21)
Biodegradable polyesters with various tacticities have been synthesized by means of stereoselective ring-opening polymerization of racemic lactide and β-lactones but with limited side-chain groups. However, stereoselective synthesis of functional polyesters remains challenging from O-carboxyanhydrides that have abundant pendant side-chain functional