Olivia Lanchoney

Chemistry and Biochemistry

Faculty Advisor: Vlad Iluc

Winter 2020-21 Project: Synthesis of a Three-Coordinate Nickel Alkylidene

A tremendous amount of research has been dedicated to the investigation of transition metal carbenes for their utility in carbon-carbon bond formation. Understanding the properties of transition metal carbenes may open new doors to the synthesis of specific organic products, such as pharmaceutical and natural compounds. Specifically, nickel carbenes are a focus of interest due to their economic advantages, non-toxic characteristics, and the rich catalytic activity of the group 10 transition metals. In this project, I aim to synthesize a three-coordinate nickel alkylidene, which has never before been synthesized. Thus far, three-coordinate nickel-carbene complexes have been synthesized but all of these examples contain either one or two aromatic substituents. [1, 2] Unlike these compounds, a nickel alkylidene would lack these electron-rich substituents, and its synthesis may provide new insight into the bonding and reactivity of nickel-carbene complexes.

[1] Daniel J. Mindiola, Gregory L. Hillhouse. Synthesis, Structure, and Reactions of a Three-Coordinate Nickel-Carbene Complex, {1,2-Bis(di-tert-butylphosphino)ethane}NiCPh2. Journal of the American Chemical Society 2002 124 (34), 9976-9977. DOI: 10.1021/ja0269183

[2]  Vlad M. Iluc, Gregory L. Hillhouse. Three-Coordinate Nickel Carbene Complexes and Their One-Electron Oxidation Products. Journal of the American Chemical Society 2014 136 (17), 6479-6488. DOI: 10.1021/ja501900j