The Chemical Synthesis Program of the Chemistry Division supports the project by Professor David Nagib of the Department of Chemistry and Biochemistry at The Ohio State University. Professor Nagib is developing new areas of synthetic chemistry that complement the methods currently used to synthesize complex organic molecules with applications ranging from pharmaceuticals and agrochemicals to biofuels and new functional materials. The goal of this research is to develop environmentally friendly catalysts using earth-abundant metals that can more easily generate a particular type of reactive intermediate known as a free radical, while also harnessing their reactivity in a controlled and selective fashion. An integral part of this program is the inclusion of underrepresented groups in this research, including high school, college, and graduate students. Professor Nagib's research team seeks to simultaneously increase interest, participation, retention, and literacy in Science, Technology, Engineering and Mathematics (STEM) fields by (a) offering hands-on research experience via a summer internship program for a diverse group of high-school and undergraduate students; (b) sharing interactive science demonstrations with local K-12 students; (c) creating informative and accessible visual media for the general public; and (d) sharing knowledge and research about radical chemistry through social media, online forums, and community outreach activities.
This integrated research, education, and outreach program is focused on enabling a complementary class of polarity-reversed, radical reactivity for carbonyls. The transformation of this ubiquitous synthetic handle from its native, electrophilic nature to an umpolung, nucleophilic ketyl radical is achieved through an anomeric activation strategy. This approach relies on in situ conversion of carbonyls to alpha-oxy intermediates, which are better suited for radical generation using mild catalysts derived from earth-abundant metals. This dual-catalytic strategy for generation of ketyl radicals is superior to current approaches that rely on strong, stoichiometric reductants to overcome the high reduction potential for single electron transfer (SET) to carbonyls. This technology has broad applicability for the development of sustainable tools for streamlining the synthesis of complex medicines and materials. Integrated outreach activities involving multimedia demonstration of the vital role of free radicals and organic chemistry in daily life is also a key aspect of this funded project.
