Grantee Research Project Results
Catalytic Arene Functionalization for Applications in Industrial Waste Reduction and Pollution SequestrationEPA Grant Number: FP917296
Title: Catalytic Arene Functionalization for Applications in Industrial Waste Reduction and Pollution Sequestration
Investigators: Thuy-Boun, Peter S
Institution: Scripps Research Institute
EPA Project Officer: Hahn, Intaek
Project Period: August 1, 2011 through July 31, 2014
Project Amount: $126,000
RFA: STAR Graduate Fellowships (2011) RFA Text | Recipients Lists
Research Category: Academic Fellowships , Fellowship - Science & Technology for Sustainability: Green Engineering/Building/Chemical Products & Processes/Materials Development
Substituted aromatic molecules are important building blocks especially common in medicine, plastics and new functional materials. Important as these compounds are, the methods employed for their construction are still indirect and often involve multiple purification steps, which can lead to the generation of large quantities of chemical waste. This research aims to streamline the synthesis of substituted aromatics through the development of catalytic direct functionalization processes.
Initially, this research will focus on elucidating Ni’s competency for catalytic C–H functionalization chemistry. Once a catalytic manifold is established, a set of ligands will be designed and screened to probe Ni’s propensity for meta/para C–H coordination and activation. Subsequently, ligands able to promote meta/para coordination will be applied under C–H functionalization conditions to achieve the selective substitution of aromatic molecules.
As Ni catalyzed C–H functionalization chemistry is relatively unexplored, it is expected that a bulk of the initial effort will be geared toward identifying compatible substrates and coupling moieties. It is likely that the substitution of aromatic compounds first will be developed using directed ortho-metalation. After a thorough understanding of this process is achieved, the research will focus on achieving meta/para activation with the application of ligands. Enhanced reactivity is anticipated with the rational modification of such ligands. A study of the structure and electronics of these ligands will provide insight for further studies potentially opening new avenues of investigation.
Potential to Further Environmental / Human Health Protection
Substituted aromatic building blocks are commonly utilized on an industrial scale. As such, the development of new greener methods for their construction has the potential to reduce the need for environmentally harmful, wasteintensive purification procedures. More efficient aromatic substitution processes also will lower the cost and broaden the diversity of building blocks used to construct medicines, biomedical materials, consumer plastics, organic light emitting diodes (OLED), organic solar cells and metal-organic frameworks (MOF) among other things. Because new functional materials such as gas sequestering MOFs rely on the availability of diverse aromatic building blocks, green technology also will benefit from more efficient aromatic functionalization methods.