Nitrogen-doped Carbon Supported Metal Catalysts for Green Organic Synthesis

Title: Nitrogen-doped Carbon Supported Metal Catalysts for Green Organic Synthesis

Speaker: Dr. Tomohiro Yasukawa, Monash University 

Abstract: Continuous-flow synthesis with heterogeneous catalysts is gaining attention for sustainable society development. These catalysts require high activity, selectivity, and durability for efficient synthesis. However, their use in organic synthesis remains limited compared to homogeneous catalysts due to analytical challenges. We focused on nitrogen-doped carbon (NDC) supports, known for their ability to coordinate and activate metal species.[1] NDC-supported metal catalysts are easily prepared via the thermal decomposition of nitrogen- and metal-containing precursors, enabling the immobilization of either metal nanoparticles or single-atoms, depending on the preparation conditions. We developed NDC-supported metal nanoparticle catalysts from polyvinylpyridine and single-atom catalysts from metal-organic frameworks to demonstrate a wide variety of organic transformations in heterogeneous manner. Notably, most reactions did not proceed without nitrogen dopant and metal leaching was suppressed in these reactions. We then demonstrated continuous-flow reactions using these catalytic reactions such as aerobic oxidation,[2] selective hydrogenation[3] and asymmetric carbene insertion.[4] Furthermore, NDC-supported catalysts were utilized as electrodes for electrochemical organic synthesis. For instance, single-zinc atom catalysts stabilized by the coordination of multiple nitrogen atoms achieved allylation of imines with allyl bromide, minimizing metal usage and leaching.[5] This reaction was successfully adapted to continuous-flow systems, achieving efficient, waste-minimized production.

References: [1] T. Yasukawa, Bull. Chem. Soc. Jpn. 2024, 97, uoae076. [2] T. Yasukawa, S. Kobayashi, et al. Catal. Sci. Technol. 2022, 12, 1043. [3] T. Yasukawa, S. Kobayashi, ACS Catal. et al. 2022, 12, 5887. [4] T. Yasukawa, S. Kobayashi, et al. Angew. Chem., Int. Ed. 2021, 60, 12786. [5] T. Yasukawa, S. Kobayashi, et al. J. Am. Chem. Soc. 2023, 145, 11939.

Bio: Dr. Tomohiro Yasukawa obtained BSc, MSc and PhD degree at The University of Tokyo, Japan in 2010, 2012 and 2015 respectively under the supervision of Prof. Shu Kobayashi. In 2013, he joined the research group of Prof. Frank Glorius at University of Münster, Germany for three month as a visiting student. In April 2015, he was appointed as a project assistant professor in Green & Sustainable Chemistry Social Cooperation Laboratory, The University of Tokyo, Japan. In October 2022, he joined the research group of Prof. Jannie Cossy at ESPCI Paris, France as a postdoc. In April 2024, he was appointed as a project assistant professor at The University of Tokyo, Japan again. In October 2024, he joined Monash University as a Lecturer.