Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 29, Issue 34, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202300494
Keywords
continuous-flow; molecular convolution; polymeric palladium catalysts; pharmaceuticals; Suzuki-Miyaura coupling
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Researchers developed a catalyst for Suzuki-Miyaura coupling under flow conditions using a molecular convolution method. The catalyst showed high performance and durability, allowing for the continuous synthesis of two pharmaceuticals in water as the sole solvent.
Given that heterogeneous palladium-catalyzed C-C bond formation reactions under continuous-flow conditions are well suited for the efficient and safe production of pharmaceuticals and functional materials, the development of active and durable catalysts for this purpose is a matter of high practical significance. Here, a previously established molecular convolution methodology was used to synthesize catalysts for Suzuki-Miyaura coupling under flow conditions by blending convoluted polymeric palladium catalysts (prepared from copolymers of 4-vinylpyridine and 4-tert-butylstyrene) and crosslinked polymeric auxiliary materials (prepared from copolymers of divinylbenzene and 4-tert-butylstyrene). The optimal catalyst exhibited high performance and durability and allowed numerous biaryl products such as liquid-crystalline materials, organic electroluminescent materials, and pharmaceuticals to be continuously synthesized with turnover frequencies of up to 238 h(-1). In a demonstration of practical utility, the developed catalytic system was used for the continuous synthesis of two pharmaceuticals (felbinac and fenbufen) in water as the sole solvent.
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