CAREER: SusChEM: Development of Tandem and Multi-Component Couplings with Base Metals and Organic Electron Donors

Project: Research project

Project Details

Description

With this CAREER Award, the Chemical Catalysis program of the Division of Chemistry is supporting the research of Professor Ramesh Giri of the University of New Mexico (UNM). The goal of this research is the development of catalytic chemical reactions using the earth-abundant and inexpensive copper (Cu) as the catalyst. The target reactions provide powerful tools for the syntheses of complex and diversified molecules, such as drugs and organic materials, by limiting the required number of reaction steps and thus minimizing the time for process development. The outcomes of this investigation have a positive impact on society by developing novel protocols for organic chemical transformations based on earth-abundant, sustainable catalysts. Professor Giri has established a partnership with the UNM College Enrichment and Outreach Program to involve undergraduates from traditionally underrepresented groups. He has established an outreach program with the South Valley Academy, a public charter school in Benalillo County, New Mexico.

Integration of cross-coupling into the tandem and multi-component (MC) reaction manifolds has the potential to create new synthetic methodologies. The research focuses on developing Cu compounds as sustainable catalysts for the proposed transformations. As part of the education component, the investigator has developed a course for senior undergraduates and graduate students focused on organometallic chemistry that emphasizes the use of sustainable transition metals in the development of new chemical transformations. In this project, various organometallic reagents, amines, alcohols, and carbonyl compounds are employed as sources of nucleophiles to add across carbon-carbon multiple bonds (olefins, alkynes, and allenes) and subsequently cross-couple with organohalides in a tandem fashion. The ability of copper to avoid beta-hydride eliminations is expected to facilitate the tandem and MC cross-couplings of electrophiles and nucleophiles that contain beta-hydrogens. Hybrid bidentate ligands containing both pi-acceptor and sigma-donor groups are employed to generate stable and active Cu in the +1 oxidation state required to conduct the proposed transformations. The ligands are tuned sterically and electronically to render Cu reactive towards the less reactive aryl halides. Alternatively, organic electron donor-based organic catalysts, which react with organohalides via a single electron transfer process, provide an alternative strategy for coupling reactions with less reactive aryl halides. A long-term goal of the project is to perform the reactions enantioselectively using chiral, non-racemic ligands to prepare complex molecules with multiple chiral centers.The research is performed at the interface of organic, inorganic and organometallic chemistry, which provides an opportunity for training future scientists from high school to graduate school. This award also supports the outreach efforts of the Giri group to train high school and undergraduate students from traditionally underrepresented groups in the sciences.

StatusFinished
Effective start/end date4/1/162/29/20

Funding

  • National Science Foundation: $675,000.00

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