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).
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 cyclisation reactions.
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