2009
DOI: 10.1039/b915669k
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Solvent-free Sonogashira coupling reaction via high speed ball milling

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Cited by 244 publications
(164 citation statements)
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“…This reaction was shown to be successful under solvent-free ball milling conditions in high yields with a Spex 8000 M vibratory mixer/mill (Scheme 15). [219] Aryl iodides and bromides gave high yields of coupling products with phenyl acetylene and trimethylsilyl acetylene using palladium tetrakis triphenyl phosphine and copper iodide as catalyst and potassium carbonate as base. Following normal reactivity trends in solution, aryl chlorides were unreactive.…”
Section: Metal-catalyzed Organic Reactions In Ball Millsmentioning
confidence: 99%
“…This reaction was shown to be successful under solvent-free ball milling conditions in high yields with a Spex 8000 M vibratory mixer/mill (Scheme 15). [219] Aryl iodides and bromides gave high yields of coupling products with phenyl acetylene and trimethylsilyl acetylene using palladium tetrakis triphenyl phosphine and copper iodide as catalyst and potassium carbonate as base. Following normal reactivity trends in solution, aryl chlorides were unreactive.…”
Section: Metal-catalyzed Organic Reactions In Ball Millsmentioning
confidence: 99%
“…2 Chemical synthesis using mechanical force, also known as mechanochemistry, 3 is a well-established field of organic synthesis. 4 In the context of organic synthesis, mechanochemistry has been demonstrated to provide a solvent-free path to a plethora of transformations, including oxidations, 5 reductions, 6 Wittig condensations, 7 palladium-catalyzed Sonogashira 8 and Suzuki couplings. 9 Recently, different research groups including Ondruschka and co-workers 10 and Bolm and co-workers, 11 have demonstrated that besides allowing solvent-free reactivity mechanochemical synthesis in a planetary mill allows substantial improvements in energy efficiency, compared to conventional solutionbased or microwave-assisted synthesis.…”
Section: Mechanosynthesis In Organic Synthesis and Cocrystallizationmentioning
confidence: 99%
“…Mechanochemistry is mainly promoted by either hand grinding or ball-milling under the solvent-free condition. Indeedly, ball-milling has already been applied for the grinding of minerals into fine particles and the preparation and modification of inorganic solids [26][27][28][29] , but more recently it has rapidly developed in the areas of organic synthesis, e.g., Suzuki [30][31][32] , Sonogashira [33][34][35] , Michael [36][37][38] , aldol reaction [39][40][41][42] , Diels-Alder reaction [43,44] , and so on. Among these, only one recent report by Stolle and co-workers [45] has addressed 1,3-dipolar cycloaddition reaction of azides with alkynes by means of ball-milling, which was named "solvent-free click reaction".…”
Section: Introductionmentioning
confidence: 99%