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The Odom Research Group is focused on several aspects of transition metal catalysis, especially those involving C–N bond formation like hydroamination and hydrohydrazination. In addition, we are interested in metal-catalyzed multicomponent couplings. Often the catalytic reactions studied involve Metal-Ligand Multiple Bond species (nitrido, oxo, imido, alkylidene, carbene, alkylidynes, carbynes, etc.) as intermediates. In cases where an organic species is sought, nitrogen-containing heterocycles are often the target.
The general goals are three fold:
(1) Discover new reactions based on transition metal catalysis
(2) Develop new catalyst architectures for known reactions with improved activity/selectivity
(3) Develop these new reactions into reliable methodologies for organic synthesis with a variety of possible applications
In accordance with the above targets, our group is comprised of what may be defined as both inorganic and organic chemists, if such designations are still meaningful, who often work together to achieve these goals. We study the electronic structure and properties of complexes relevant to the reactions, design and try new catalyst architectures, and develop new methodologies for organic synthesis.
From an application standpoint, the methodologies being developed are new routes to heterocyclic compounds, which include quinoline, pyrimidine, and pyrazole frameworks among others.
We are currently examining the applications of these methodologies for kinase inhibitors, natural product synthesis, and organic dyes for Dye-Sensitized Solar Cells.
A brief description of recent past and current research is found below. Some of the topics have links to additional information. More will be coming as the chemistry develops, and as we manage to get synopses written. As always, feel free to contact us for additional info.
Alkyne Iminoamination
This reaction is a titanium-catalyzed multicomponent coupling reaction based on the alkyne hydroamination catalytic cycle. The reaction involves the 3-component coupling between an alkyne, isonitrile, and primary amine to generate derivatives of 1,3-diimines. This process can be coupled to one-pot syntheses of heterocycles. In other words, we are studying generation of substituted heterocycles from a multicomponent coupling reaction followed by addition of an additional reagent in this research.
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Catalyst Parameterization
In this project, we are examining the use of high oxidation state complexes for parameterizing ligand donor ability in d0 metal complexes. There are many well-known reactions where the donor ability of ancillary ligand sets affect the overall catalytic activity of a compound. However, it can be difficult to evaluate the donor abilities of structurally diverse ligands, e.g., pyrrolyl versus phenoxides. Here, we are trying to experimentally identify the donor ability of ligands and correlate that donor ability to spectroscopic measurements and reactivity in a diverse array of early transition metal systems.
Hydrohydrazination and Iminohydrazination
Our group was one of the first to report the catalyzed addition of hydrazines to C–C unsaturated compounds, or hydrohydrazination. These reactions are now known to be catalyzed by several transition metals; however, the titanium-based catalyst structures are still some of the most versatile and are applicable to both internal and terminal alkynes with mono- and disubstituted hydrazines. The products are hydrazones that may be isolated on their own for further reactivity, or the hydrazones can be converted directly to indoles using an acid or Lewis acid. In related chemistry, titanium complexes will catalyzed the 3-component coupling reactions between 1,1-disubstituted hydrazines, alkynes, and isonitriles.
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N–N Bond Cleavage and N–N Bond Formation Mechanisms
We are currently also investigating new mechanisms for N–N bond cleavage reactions possibly of relevance for nitrogenase or Haber-Bosch nitrogen reduction, and we are interested in reactions for their microscopic reverse as well where N–N bonds are formed.
Unique Metallacycles Containing Alkylidenes
We have also examined synthetic routes to unique metallacyclic derivatives of Group-6 alkylidenes and their reactivity. Some of these compounds have potential applications as surrogates for more costly to prepare discrete alkylidenes, such as Schrock’s catalyst. Also, we have generated metallacyclic derivatives of Schrock’s catalyst with potentially interesting polymerization properties.
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The Graduate Program in Chemistry at Michigan State University
