The Suzuki−Miyaura Reaction under Mechanochemical Conditions

Abstract

As a model for a C−C-coupling procedure a Suzuki−Miyaura reaction has been studied under mechanochemical conditions. Important parameters influencing the yield of the reaction are the revolutions per minute, the milling time, and the material of the milling balls and beakers, as well as the size and number of milling balls.

Mechanochemistry: opportunities for new and cleaner synthesis

“…[222] The system requires a stoichiometric amount of tetraalkylammonium salt but is both solvent-and phosphine-free. Recently, Ondruschka and coworkers [224] found that potassium carbonate (base) and sodium chloride Ondruschka also found that under ball milling conditions aryl bromides were more reactive than aryl iodides, which contrasts with Suzuki reactions in solvents. It was also found that the greater water content of the alumina, the greater the reaction.…”

CHAPTER 10. Technical Implications of Organic Syntheses in Ball Mills

“…62,70 However, there are also examples from the field of organic synthesis in which no influence was observed, which seems to indicate a product decomposition due to high energy. 60,66,72,73 Table 10.1 provides an overview of the materials for milling balls and milling vessels applicable for mechanochemical syntheses. Beside material density, the chemical resistance is also important for organic syntheses.…”

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

“…Based on our knowledge, some examples of the preparation of Pd supported catalysts by mechanochemical activation are reported in Table 8. [153] Examples in the literature also address the topic of using mechanochemical activation in solvent free SMC [154,155]. Cravotto et al have reported the use of a new catalyst, based on chitosan that is cross-linked with hexamethylene diisocyanate using Pd(OAc) 2 , in solid-state SMC with aryl chloride.…”