Jamison Nickel (II) Precatalysts

Introduction

Nickel catalysis has broad synthetic utility. However, the dearth of bench-stable nickel(0) sources and high catalyst loadings have limited its use.¹ The Jamison group has developed a library of bench-stable phosphine-containing nickel(II) precatalysts that are converted into active catalysts in situ.^2,3

Figure 1. Nickel catalysis has broad synthetic utility

Advantages

• Air- and water-stable
• Converted to the active catalyst in situ
• Can be used under ambient conditions – glovebox not necessary

Figure 2. Representative Application²

Materials

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References

1. Tasker SZ, Standley EA, Jamison TF. 2014. Recent advances in homogeneous nickel catalysis. Nature. 509(7500):299-309. https://doi.org/10.1038/nature13274

2. Standley EA, Jamison TF. 2013. Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes. J. Am. Chem. Soc.. 135(4):1585-1592. https://doi.org/10.1021/ja3116718

3. Standley EA, Smith SJ, Müller P, Jamison TF. 2014. A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes. Organometallics. 33(8):2012-2018. https://doi.org/10.1021/om500156q