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28-0165: New Nickel Precatalyst for Cross-Coupling Reactions

Air and Moisture Stable Nickel Precatalyst with Good Solubility in Organic Solvents for Screening of Cross-Coupling Reactions

Strem is pleased to introduce a new Nickel (II) precatalyst for use in cross-coupling and cyclization reactions.

The precatalyst is a TMEDA stabilized Nickel (II) compound derived from the oxidative insertion of Nickel into the carbon-chloride bond of 2-chlorotoluene (28-0165).

28-0165

The solid material is reasonably air-stable.  Furthermore, it is also stable for at least 24 hours in a variety of common organic solvents when kept under nitrogen, which allows for the preparation of stock solutions for use in high-throughput experimentation.

The absence of Phosphine ligands and the easy replacement of TMEDA make the product an ideal Nickel source.  A large number of reaction conditions can be screened by substituting TMEDA with other ligands.

Compared with other common Nickel sources for cross-coupling the new precatalyst gives good to excellent yields in Suzuki, Heck, Kumada, Negishi and Buchwald-Hartwig amination, borylation, reductive coupling and cyclization reactions.

This new Nickel compound has the potential to replace some Palladium catalysts in a variety of reactions and is a useful addition in the quest to replace higher cost precious metals with abundant, lower cost first row transition metals in catalytic reactions.

References:

1. ACS Catalysis,  2015, 5, 3120-3123                                        

2. Org. Lett., 2015, 17, 2166-2169

 

Product mentioned in this blog:

28-0165: Chloro(2-methylphenyl)(N,N,N,N-tetramethyl-1,2-ethylenediamine)nickel(II), 99% (contains about 5% o-chlorotoluene) NiCl(o-tolyl)(TMEDA)

 

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