Palladium-Catalyzed Mechanochemical Cross-Coupling Reactions

In this thesis, the author developed cross-coupling reactions that proceed in the solid state without using organic solvents, utilizing a mechanochemical synthesis method using a ball mill. Compared to conventional solution systems, the reactions realized a drastic reduction of chemical waste, a drastic acceleration of chemical reactions, and efficient transformations of insoluble compounds. The thesis demonstrates that mechanochemical synthesis method has the potential to revolutionize organic synthesis. Readers can learn not only about mechanochemical synthesis but also about new reactions and syntheses of new compounds that could not be obtained under solution conditions. Recently, mechanochemical synthesis has become increasingly popular among a wide range of researchers as an environmentally friendly and highly efficient method, so this thesis has a timely publication.

1. General Introduction.- 2. Olefin Accelerated Solid State C N Cross Coupling Using Mechanochemistry.- 3. Solid State Suzuki-Miyaura Cross Coupling Reactions Using Mechanochemistry.- 4. Tackling Solubility Issues in Organic Synthesis: Solid State Cross Coupling of Insoluble Aryl Halides.- 5. Solid State Cross Coupling Reactions of Insoluble Aryl Halides Under Polymer Assisted Grinding Conditions.- 6. Mechanochemistry Directed Ligand Design: Development of a High Performance Phosphine Ligand for Palladium Catalyzed Suzuki Miyaura Cross Coupling Reactions.- 7. Mechanochemical Monoarylation of Dihaloarenes Enabled by In Situ Crystallization.- 8. Metallamechanoredox: Force induced Nickel Catalyzed Arylamination Using Ball Milling and Piezoelectric Materials.

Tamae Seo received a Ph.D. in engineering from Hokkaido University in 2023. Her research field was organic synthesis, and particularly she was engaged in research on palladium-catalyzed cross-coupling reactions using mechanohemistry. She has published 13 papers about mechanochemical reactions, and these papers demonstrated that the mechanochemical synthesis method has the potential to revolutionize organic synthesis. She has received many awards for presentations at academic conferences, and in 2023 she won the L’Oréal-UNESCO For Women in Science Japan Fellowship Award.