244988

Sigma-Aldrich

双(1,5-环辛二烯)镍(O)

别名:
双-(1,5-环辛二烯)镍, Ni(COD)2
Empirical Formula (Hill Notation):
C16H24Ni
CAS号:
分子量:
275.06
EC 号:
MDL编号:
PubChem化学物质编号:

质量水平

200

reaction suitability

core: nickel
reagent type: catalyst

mp

60 °C (dec.) (lit.)

储存温度

−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

应用

作为下列反应的反应物:
  • 氧化加成反应

作为下列反应的催化剂:
  • 酮与氯代芳烃的非对称α-芳基化和杂芳基化
  • 交叉偶联反应
  • 烯丙基醛在二氧化碳气氛中的区域选择性和立体选择性羧化/环化
  • 均相炔醇的甲基羧化
  • 立体选择性硼环化酮-二烯偶联
  • 苯甲酰胺与内部炔烃的环加成反应
用于催化烯丙基苯基硫醚加成到炔烃,生成 1,4-二烯类化合物。与末端炔烃的反应以高产率和高选择性进行。可连接多种官能团。
用于 1,3-二烯类化合物环加成的催化剂。

包装

2 g in glass bottle

警示用语:

Danger

hazcat

Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1

靶器官

Lungs

storage_class_code

4.1B - Flammable solid hazardous materials

WGK Germany

WGK 3

闪点(F)

Not applicable

闪点(C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

分析证书

原产地证书 (CofO)

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...
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...
Ruimao Hua et al.
Organic letters, 9(2), 263-266 (2007-01-16)
Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate...
Joachim Loup et al.
Angewandte Chemie (International ed. in English), 58(6), 1749-1753 (2018-12-06)
Highly enantioselective nickel-catalyzed alkene endo-hydroarylations were accomplished with full selectivity by organometallic C-H activation. The asymmetric assembly of chiral six-membered scaffolds proved viable in the absence of pyrophoric organoaluminum reagents within an unprecedented nickel/JoSPOphos manifold.
Journal of the American Chemical Society, 111, 6432-6432 (1989)
技术文章
Csp2- and Csp-hybridized coupling reactions are established catalytic approaches. However, multi-step Csp3- and Csp2-coupling reactions of boronic acids and related derivatives are still limited by ineffective two-electron transmetalation reactions.
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