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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.