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Sigma-Aldrich

Ni(COD)(DQ)

≥95%

Synonym(s):

Bis(1,5-cyclooctadiene)(duroquinone) nickel(0)

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About This Item

Empirical Formula (Hill Notation):
C18H24NiO2
CAS Number:
40759-64-6
Molecular Weight:
331.08
UNSPSC Code:
12352103
NACRES:
NA.22

Quality Level

100

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

parameter

temperature stable

mp

227 °C (decomposition)

Application

Ni(COD)(DQ), as shown by the Engle lab, is an air- and thermally stable Ni(0) precatalyst. This 18-electron complex has a unique stability profile allowing for easy reaction setup outside an inert atmosphere. Transformations such as the Suzuki-Miyaura coupling, borylation of aryl halides, and alkene hydroarylation have been demonstrated.

Other Notes

Ni(COD)(DQ): An Air-Stable 18-Electron Ni(0)–Olefin Precatalyst

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Description
Pricing

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Lungs

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

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Van T Tran et al.
Angewandte Chemie (International ed. in English) (2020-02-18)
We report that Ni(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature. Due to its apparent stability, use of Ni(COD)(DQ) as a

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Engle Group – Professor Product Portal

The Engle lab strives to invent novel catalytic alkene and alkyne functionalization methods to expedite organic synthesis. These transformations offer a powerful platform for conversion of simple, abundant, and planar starting materials into densely functionalized, stereochemically complex products in a single step. To this end, the Engle lab has developed various substrate directivity strategies in which native functional groups can be temporarily masked with auxiliaries that are capable of reversibly binding the metal catalyst, thereby enhancing kinetic reactivity, suppressing unwanted side reactions, and facilitating high selectivity. The Engle lab works with us to make synthetically enabling directing groups, catalysts, and ligands readily available to the synthetic community for reaction discovery and small-molecule synthesis.

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