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912794

Sigma-Aldrich

Ni(COD)(DQ)

≥95%

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Synonym(s):
Bis(1,5-cyclooctadiene)(duroquinone) nickel(0)
Empirical Formula (Hill Notation):
C18H24NiO2
CAS Number:
Molecular Weight:
331.08

Quality Level

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

227 °C (decomposition)

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244988927082213934
Ni(COD)(DQ) ≥95%

912794

Ni(COD)(DQ)

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

244988

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

Ni(COD)(Cy-BQ) ≥95%

927082

Ni(COD)(Cy-BQ)

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

reaction suitability

-

reaction suitability

-

reaction suitability

-

form

powder

form

-

form

powder

form

solid

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

mp

227 °C (decomposition)

mp

60 °C (dec.) (lit.)

mp

-

mp

206-209 °C (lit.)

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.

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Description
Pricing

pictograms

Exclamation markHealth hazard

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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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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