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Polystyrene-Cross-Linking Triphenylphosphine on a Porous Monolith : Enhanced Catalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow

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Title: Polystyrene-Cross-Linking Triphenylphosphine on a Porous Monolith : Enhanced Catalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow
Authors: Matsumoto, Hikaru Browse this author
Hoshino, Yu Browse this author
Iwai, Tomohiro Browse this author
Sawamura, Masaya Browse this author →KAKEN DB
Miura, Yoshiko Browse this author
Issue Date: 26-Aug-2020
Publisher: American Chemical Society
Journal Title: Industrial & engineering chemistry research
Volume: 59
Issue: 34
Start Page: 15179
End Page: 15187
Publisher DOI: 10.1021/acs.iecr.0c02404
Abstract: Immobilized transition metals for continuous-flow catalyses are greatly in demand to achieve automation, scale-up, facile separation, regeneration, and energy-saving production with high level of sustainability and efficiency. Here, we report a tertiary phosphine immobilized on a macroporous monolith (M-PS-TPP) for the challenging Pd-catalyzed cross-coupling reaction of aryl chloride in a continuous-flow system. The monolithic and macroporous structure of M-PS-TPP was fabricated by bulk polymerization in the presence of a high internal phase emulsion (HIPE) template. Owing to the large pore size and high porosity, the M-PS-TPP showed high permeability against continuous flow of the mobile phase. The continuous-flow Suzuki-Miyaura cross-coupling reaction was realized by permeation of organic/aqueous media containing inorganic salt through a Pd-loaded monolith (M-PS-TPP-Pd) column without serious clogging. Controlling coordination chemistry and hydrodynamics of M-PS-TPP-Pd boosted highly active phosphine-metal complex formation and fast mass transfer of reactants. Indeed, the M-PS-TPP-Pd column showed surprisingly higher yields (similar to 93%) and turnover numbers (2704) under continuous-flow conditions than that under batch conditions (similar to 6%).
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Industrial and Engineering Chemistry Research , copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 澤村 正也

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