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  • Professor Peter Zhang
    03/03/20 - 9:45 AM to 11:00 AM

    Student Seminar Series: Professor X. Peter Zhang

    Student Seminar Series

Metalloradical Catalysis for Stereoselective Radical Reactions

Organic synthesis has been dominated by the development of chemical reactions that are based on two-electron heterolytic ionic processes, either stoichiometrically or in catalytic fashion. While one-electron homolytic radical chemistry is equally rich and has been demonstrated with a number of unique features, its application in practical synthesis of organic molecules has been hampered by several enduring challenges. Over the past two decades, my laboratory has been in the process of formulating “Metalloradical Catalysis” (MRC) as a general concept to guide the development of fundamentally new approaches for controlling both reactivity and stereoselectivity of radical reactions. In essence, metalloradical catalysis aims for the development of metalloradical-based systems for catalytic generation of carbon- and nitrogen-centered radicals from common organic compounds without the need of radical initiators or the use of light. The subsequent reactions of the resulting organic radical intermediates, which remain covalently bonded or closely associated with the metal center, can be selectively controlled by the catalyst. For achieving enantioselective radical reactions via MRC, we have developed a family of unique chiral metalloradical catalysts based on structurally well-defined Co(II) complexes of D2-symmetric chiral porphyrins with tunable electronic, steric, and chiral environments. These Co(II)-based metalloradical catalysts have been shown to be highly effective for a wide range of stereoselective organic reactions, including olefin cyclopropanation, olefin aziridination, C–H alkylation and C–H amination. Due to their distinctive radical mechanisms that involve unprecedented α-metalloalkyl and α-metalloaminyl radical intermediates, the Co(II)-based metalloradical systems enable addressing some long-standing problems in these important organic transformations.

Professor Peter Zhang's graphic for his research on formulating “Metalloradical Catalysis” (MRC) guiding the development of fundamentally new approaches for controlling reactivity and stereoselectivity of radical reactions.

Research

Professor Zhang's research program has centered on the development of fundamentally new catalytic systems for stereoselective chemical transformations and their applications for practical synthesis of organic molecules. Researchers in his group are particularly interested in developing one-electron catalytic approaches for homolytic radical chemistry to harness the vast potential of radical reactions for stereoselective construction of molecular structures. To this end, They have formulated “Metalloradical Catalysis” (MRC) as a concept to guide the development of general approaches for controlling reactivity and selectivity of various radical processes. For achieving enantioselective radical reactions, they have developed a family of unique chiral metalloradical catalysts based on structurally well-defined Co(II) complexes of D2-symmetric chiral porphyrins with tunable electronic, steric, and chiral environments. These Co(II)-based metalloradical catalysts have shown to be highly effective for a wide range of stereoselective organic reactions. Due to their distinctive radical mechanisms that involve unprecedented metal-stabilized radical intermediates, such as α-metalloalkyl radicals (also known as metallocarbene radicals) and ɑ-metalloaminyl radicals (also known as metallonitrene radicals), the Co(II)-based metalloradical systems enable addressing some long-standing challenges in these important organic transformations.

Professor Zhang

Professor Zhang earned his bachelor's degree from Anhui Normal University in China, his master's degree from Beijing Normal University in China, and his doctorate from the University in Pennsylvania. He was a post-doctoral researcher at the Massachusetts of Technology. Prior to joining the chemistry faculty at Boston College in 2015, he was a professor at the University of Tennessee and University of South Florida.

  • Event Details

    Location: 331 Smith Hall
    Host: Samantha Apps
    Speakers:
    • Professor X. Peter Zhang
    • Peter Zhang
    • Department of Chemistry
    • Boston College

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