SusChEM: Selective C-H Functionalization by Highly Tunable Metalloporphyrin Carbenoid: A Mechanistic Investigation

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The Division of Chemistry supports the efforts of Professor Yong Zhang of the Stevens Institute of Technology towards selective carbon-hydrogen (C-H) functionalization using metalloporphyrin carbenoids. Metalloporphyrin carbenoids have been found to be among the most efficient and selective catalysts for C-H insertions however, mechanistic studies on these catalysts are relatively scarce and the origins of molecular reactivity and selectivity have not been well characterized. Such information is critical for the future development of these catalysts, especially since most reported C-H insertion yields are modest. Dr. Zhang's research provides systematic profiles of the origins of reactivity for key metalloporphyrin carbenes as well as reactivity and selectivity trends of various structural factors to facilitate the development of highly selective metalloporphyrin-based C-H insertion catalysts with metal centers that are earth-abundant, minimally toxic, and relatively inexpensive. Dr. Zhang's research is broadly integrated with teaching and learning. Students in his lab are actively involved in classes and outreach programs that incorporate their research results. Dr. Zhang continues his vigorous efforts to have broad participation of students from different groups at various levels, particularly including students from underrepresented groups. Organic synthesis is of vital importance in modern society to provide drugs and materials. Selective carbon-hydrogen (C-H) functionalization represents a powerful, potentially sustainable strategy for organic synthesis. As models of broadly interesting and useful heme protein reaction intermediates, metalloporphyrin carbenoids have been found to be among the most efficient and highly selective catalysts for C-H insertions into organic molecules, even though few mechanistic studies have been done and their origin of the catalyst's reactivity and selectivity are not clear. Such information is critical for future development, especially since most C-H insertion yields using these catalysts are modest. Dr. Zhang's research provides systematic profiles of needed information such as molecular design guidelines to facilitate the development of highly selective metalloporphyrin-based C-H insertion catalysts that use earth-abundant metals (such as iron). Such insights may lead to improvements sustainable and "green" chemistry in the pharmaceutical and materials syntheses industries. Dr. Zhang's research is broadly integrated with teaching and learning. Several channels are employed by his students to broadly disseminate their research to the scientific community and general public. For example, students involved in this NSF-supported project are required to give presentations/reports in their classes, and within their department, university, K-12 institutions, museums, news media, and/or other venues, enhancing the scientific understanding of the impacts of this project.