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Suzuki-Miyaura coupling catalyzed by various Pd(II) catalysts under mechanochemical conditions

Palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with organoboron reagents is one of the simplest and most widely used approaches for the preparation of biaryls, which are important structural units in natural products, pharmaceuticals, and advanced materials. Since the traditional Suzuki–Miyaura coupling procedure involves the use of palladium catalysts with phosphine ligands, which are toxic and sensitive to air and moisture, the development of efficient and phosphine-free systems for these reactions under mild conditions is of current interest. In this work, a model Suzuki-Miyaura cross-coupling reaction between 4-bromoazobenzene and phenylboronic acid was carried out under mechanochemical conditions to compare the catalytic potential of various commercially available Pd(II) catalysts and prepared phosphinefree palladacycles of azobenzene. In situ Raman monitoring of these reactions provided direct insight into the dynamics of formation of the products and optimization of factors controlling reactivity.

Suzuki-Miyaura reaction ; Palladium ; Mechanochemistry ; Solid-state ; Catalysis

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