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28-0040 a new air and temperature stable Nickel(0) starting material

(COD)(duroquinone) nickel(0) as a source for Nickel (0) that can be conveniently used outside the glovebox

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Figure 1. 28-0040 (1,5-Cyclooctadiene)(duroquinone) nickel(0), min. 98%

(1,5-Cyclooctadiene)(duroquinone) nickel(0) (Ni(COD)(DQ)) was initially reported in the early 1960s (Ref. 1), long before any modern cross coupling reactions were developed. For many years, the complex was not adopted for wider use in catalytic nickel chemistry. Recently, however, Professor Keary Engle from the Scripps Research Institute has begun to deploy Ni(COD)(DQ) with great success as a starting material which provides a precatalytic source of Ni(0). (Ref. 2).

Ni(COD)(QD) (28-0040) is an 18-electron Ni0-olefin complex with great similarities to Ni(COD)2. The Nickel (0) atom is stabilized by two pairs of olefinic double bonds provided by the 1,5-cyclooctadiene and duroquinone ligands. The two sets of double bonds are orthogonal and form a tetrahedral arrangement around the central nickel atom. However, unlike Ni(COD)2, this compound can be stored for a prolonged period at room temperatures and  stable to air and moisture.

For more information, please read the beautifully worded review “Nickel Don’t Care About No Air” in Nature Reviews Chemistry (Ref. 3).

Professor Engle’s group showed that Ni(COD)(DQ) is an effective precatalyst in a variety of synthetic methods including Suzuki-Miyaura cross coupling reactions and amination of aryl chlorides.

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A very exciting new reaction was recently developed by chemists from Merck (ref. 4): 28-0040 was used as a precatalyst for C-CN bond activation in late-stage carbon isotope exchange of aryl nitriles. This is the first carbon isotope exchange method for nitriles, and it was demonstrated on more than 30 examples including the 14C labeling of the HIF-2α inhibitor Belzutifan.

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We are excited to offer this new Strem item (28-0040) in high chemical purity (>98%)  to scientists working in the field.

 

References:

1. Naturforsch. B, 1962, 17, 73-76.

2. Angew. Chem. Int. Ed., 2020, 59, 7409 -7413.

3. Nature Reviews Chemistry, 2020, 4, 171.

4. J. Am. Chem. Soc. 2021, 143, 12, 4817–4823.

 

Featured Product:
28-0040 (1,5-Cyclooctadiene)(duroquinone) nickel(0), min. 98% (40759-64-6)

 

Related Materials:
Technical Note
Catalysts & Chiral Catalysts
Metal Catalysts for Organic Synthesis

 

 

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