CAREER: New Reagents and Strategies for Catalytic Nucleophilic Fluorination

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With this CAREER Award, the Chemical Synthesis Program is supporting the research of Professor Abigail G. Doyle of Princeton University to invent new reagents and strategies for nucleophilic fluorination. The first objective of this research is to develop Lewis base-catalyzed hydrofluorinations using benzoyl fluoride as a latent fluoride source. The second objective is to design catalytic methods for the regio- and stereoselective synthesis of allylic and benzylic fluorides. The research is expected to facilitate the discovery and manufacture of pharmaceutical agents, agrochemicals, and functional materials by enabling the preparation of novel fluorinated building blocks using inexpensive and readily available fluoride sources. Knowledge accrued through these investigations should give way to a better understanding of the impact of aliphatic fluorine substitution in biomedical and basic research and afford new opportunities for reaction design. Professor Doyle will also be initiating educational outreach projects that interweave research and teaching. The impact of the education plan will be to broaden participation in STEM fields, particularly by underrepresented minorities and women, through early engagement of these students in hands-on research activities. One program involves providing students from a Trenton-area community college that serves a diverse population, including underrepresented minorities and low-income students, the opportunity to pursue research as part of their honors chemistry curriculum in Professor Doyle's laboratory. Second, the student invited lecture series at Princeton will be expanded to include speakers from industry, primarily undergraduate institutions, and government agencies to expose students to more varied career opportunities in the STEM disciplines.