Mechanochemical Cross-Coupling Reactions

Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki–Miyaura cross-coupling reactions

“…3 f Interestingly, Buchwald and other researchers have demonstrated that some of these transformations can be conducted at low catalyst loadings, 4 a room-temperature, 4 b short reaction times, 4 c using green solvents, 4 d , e and deactivated substrates. 4 f – h Other advancements and green approaches that have been demonstrated with dialkylbiaryl phosphines include flow chemistry, 4 i , j solvent-free reaction conditions, 4 k and mechanochemically processes (ball milling). 4 l The effectiveness of the well-known dialkylbiaryl phosphines is believed to arise from the electron-rich and sterically hindered characteristics of the dialkyl substituents on the phosphorus atom.…”

Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC2

“…The protocol expands the scope of the mechanochemical Sonogashira cross-couplings developed by Mack and Stolle and highlights the benefits of ball milling compared to solution-based reactions of poorly soluble substrates. See: Gao, Y.; Feng, C.; Seo, T.; Kubota, K.;Ito, H. Chem. Sci.…”

“…1 In the last 20 years, features such as shorter reaction times, environmental advantages, and variation in reactivity and selectivity compared to solvent-based protocols moved mechanochemistry more into the focus of various fields of chemistry. 2,3 Reactions are induced by energy transfer through shearing, pulling, and compression of material. In the simplest case the reaction is conducted by grinding with mortar and pestle.…”

“…Mechanochemical conditions have been successfully applied to important cross-coupling reactions such as Suzuki-Miyaura, Negishi, Mizoroki-Heck, and Sonogashira couplings. 3 In 2009 Mack and co-workers reported the first Sonogashira cross-coupling reaction under mechanochemical conditions performed in a mixer mill to construct diarylethynes or 1-aryl-2-(trimethylsilyl)acetylenes (Scheme 1). 4 The use of copper salt could be omitted using a jar or balls made of copper.…”

Cu salts-free mechanochemical approach towards multi-functionalized 1,2,3-triazoles and anti-seizure drug Rufinamide analogs

“…41 Complementing solution-based synthesis, the mechanochemical operations provide an environmentally benign alternative to negate the demand for bulk organic solvents thereby found its application in a plethora of organic transformations. [42][43][44][45][46][47][48] In broader sense, the application of mechanical energy such as compression, shearing or friction under solvent free conditions have been a promising technique for the utilization of mechanoresponsive materials to access active pharmaceutical ingredients (API) and thereby making a strong impact for pharma industries. 49 This technique also provides a cleaner source of energy for the organic transformations.…”