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Ni(COD)2 60+ Years – Still an Effective Source of Ni(0) in Organometallic Chemistry

28-0010 Bis(1,5-cyclooctadiene)nickel(0) is the most widely used precursor for applications in the synthesis of Nickel (0) compounds

Bis(1,5-cyclooctadiene) nickel(0) (28-0010), commonly referred to as Ni(COD)2, is an 18-electron d-10 complex consisting of a Ni(0) center supported by two cyclooctadiene ligands. The complex was originally reported in 1960 by Prof. Guenther Wilke1 and adopts a pseudo-tetrahedral arrangement of olefin C=C bonds around the Ni center.2 Owing to its fully populated d-orbitals, Ni(COD)2 is a diamagnetic species readily characterized by NMR spectroscopy.3


Since its initial discovery, bis(1,5-cyclooctadiene) nickel(0) (28-0010) has seen widespread use in a variety of chemical reactions over the last 60 years. This is due mainly to the solubilizing effect of the 1,5-cyclooctadiene ligands, which greatly increase the solubility of the complex in organic solvents, as well as their lability, allowing the COD ligands to quickly be replaced by other ligands in solution. Taken together, Ni(COD)2 provides a powerful delivery system for Ni(0) into a catalytic system without the need for additional activation steps (i.e. through reduction of Ni(II) compounds). In SciFinder, the number of reactions in which Ni(COD)2 plays a role exceed 100,000 reports, further illustrating the ubiquity of this complex. A few prototypical examples of Ni(COD)2 being used in situ to aid in the formation of Ni(L)n compounds are shown below .4-6


Although the cyclooctadiene ligands of Ni(COD)2 enable the complex to function as a highly effective precatalyst, they also lead to increased susceptibility to decomposition pathways such as oxidation. This necessitates that the complex be stored under an inert atmosphere at low temperatures. Similar to other organometallic complexes such as Pd(PPh3)4, one can use the color of the material as a form of quality control: High quality, pure Ni(COD)2 is characterized as a bright yellow powder. However, when the complex begins to decompose it can take on a dark yellow-brown color, with further degradation leading to green coloration.7


With the recent push for using abundant, cost-effective metals in catalysis, nickel provides an attractive alternative to its heavier second and third row transition metal counterparts. Strem offers high purity bis(1,5-cyclooctadiene) nickel(0) (28-0010), as well as a host of other nickel complexes and ligands tailored specifically for nickel chemistry.8 In addition, a number of alternative Ni(0) starting materials to suit a variety of research needs are currently in development.


1. Angewandte Chemie 1960, 72, 581.

2. Kristallograp. Kristallgeom. Kristallphys. Kristallchem. 1965, 122, 1.

3. Inorg. Synth. 1990, 28, 94.

4. J. Am. Chem. Soc. 2008, 130, 12874.

5. Science 2014, 345, 433.

6. Nature 2020, 586, 242.

7. Angew. Chem. Int. Ed. 2020, 59, 7409.

8. Nat. Chem. 2017, 9, 779.


Featured Product

28-0010 Bis(1,5-cyclooctadiene)nickel (0), 98+% (1295-35-8)

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