To realize the Suzuki-Miyaura cross-coupling reaction using insoluble aromatic halides as a reaction substrate, we have established a synthetic method called high-temperature ball milling, in which ball milling is performed while heating with a heat gun. The reaction was applied to insoluble pigments and dyes, which could not be handled by conventional methods due to their extremely low solubility and gave the desired coupling products. These results are expected to lead to the development of new chemical products, pharmaceuticals, organic light-emitting materials, and organic electronic materials that could not be synthesized by conventional organic synthesis in solution.
Establishment of a high-temperature ball milling while heating with a heat gun, and success in solid-state cross-coupling reactions of insoluble compounds
Original paper:
Kubota, Ito et al., Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides. Journal of the American Chemical Society, March 30, 2021. DOI:10.1021/jacs.1c00906