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Polystyrene-Cross-Linking Triphenylphosphine on a Porous Monolith : Enhanced Catalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow
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 https://pubs.acs.org/doi/10.1021/acs.iecr.0c02404. |
Type: | article (author version) |
URI: | http://hdl.handle.net/2115/82329 |
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)
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Submitter: 澤村 正也
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