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Current Research Projects

1. Reactions of Aryl Chlorides Using Palladium Catalysts: Mechanistic Studies


Aryl chlorides such as 1 are useful intermediates in synthetic organic chemistry. However, they are also long-lived and extremely toxic pollutants of soil, surface water, and ground water, in the form of PCB’s and dioxins, as exemplified by 2 and 3.

One long-term goal of this project is to develop methodology for palladium-catalyzed hydrodechlorination of aryl chlorides that could be applied to soil and water remediation in areas of PCB and dioxin contamination. We have recently found that aryl chlorides are easily reduced in hot methanol using the Buchwald palladium catalyst, and sodium formate as the reducing agent.[1] The starting materials were five commercially available aryl chlorides (not PCB's or dioxins!). We are currently interested in establishing the nature of the active palladium catalyst, extending its use to reaction conditions that are more environmentally friendly, such as water or ionic liquids, and exploring the possibility of extracting organic products into supercritical CO2. A student working on this project would gain experience in several areas:

  • The synthesis and purification of organic compounds.
  • Using gas chromatography and NMR spectroscopy to follow reaction progress.
  • Obtaining and using spectral data, including nuclear magnetic resonance spectral data, to evaluate the structures and purity of organic reaction products.

In the context of this project, a student would gain experience in searching the chemical literature, planning and executing experiments, recording and interpreting scientific data, and reporting scientific results.

[1] Logan, M. E.; Oinen, M. E. Organometallics, 2006, 25, 1052-1054.


2. The Synthesis of Water-Soluble Dye Precursors: Novel Julolidine Derivatives

The electron-rich aniline julolidine (2,3,6,7-tetrahydro-1H,5H-benzo(i,j)quinolizine) is an important component of dyes used in a variety of applications, including molecular rotors, and near-infrared dyes. Julolidine, or 2,3,6,7-tetrahydro-1H,5H-benzo(i,j)quinolizine, is a derivative of aniline in which the nitrogen is connected to the ortho positions of the aromatic ring through chains consisting of three methylene groups. Its utility in dyes is due to the enforced overlap between the aniline nitrogen lone pair and the aromatic ring (because the nitrogen is connected to the ortho positions of the aromatic ring through chains consisting of three methylene groups). This leads to dyes with longer wavelength and greater molar absorptivity. Given that many dye applications (such as those in biological systems) require water-solubility, it would be useful to prepare water-soluble julolidine dyes. However, solubilizing groups attached to the carbons of the julolidine aromatic ring tend to create steric problems resulting in poor dye properties. Therefore, our goal is to synthesize water-soluble julolidine compounds with one or more carboxylate ion groups on one of the methylene groups connecting the nitrogen to the aromatic ring, where it would not be expected to change the dye properties. We have made some progress toward the synthesis, but more work is required to complete it, and for the preparation to be efficient, leading to the product in high yield and purity. In addition, the incorporation of the water-soluble julolidine into several dyes would demonstrate its utility.

A student working on this project would gain experience in several areas:

  • The synthesis and purification of organic compounds.
  • Using gas chromatography and NMR spectroscopy to follow reaction progress and evaluate product purity.

In the context of this project, a student would gain experience in searching the chemical literature, planning and executing experiments, recording and interpreting scientific data, and reporting scientific results.