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Durable Heterogeneous Pd-PNP Pincer Complex for CarbonCarbon Bond Formation in Continuous-Flow Systems.

Naoya Sakurada1, Kanon Kawai1, Yuka Abe1

  • 1Laboratory of Advanced Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu, 501-1196, Japan.

Chemsuschem
|August 30, 2025
PubMed
Summary

A new palladium catalyst, Pd-SCORPI, shows excellent stability and efficiency in continuous-flow carbon-carbon coupling reactions. This durable heterogeneous catalyst offers high yields and recyclability, advancing green chemistry for industrial applications.

Keywords:
Mizoroki–Heck reactionsSuzuki–Miyaura couplingcontinuous‐flow reactionsheterogeneous catalysispalladium

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Area of Science:

  • Catalysis
  • Green Chemistry
  • Organic Synthesis

Background:

  • Developing stable and recyclable catalysts is crucial for sustainable chemical synthesis.
  • Heterogeneous catalysts offer advantages in separation and reusability compared to homogeneous counterparts.
  • Palladium-catalyzed cross-coupling reactions are fundamental in organic synthesis but often face challenges with catalyst stability and efficiency in flow systems.

Purpose of the Study:

  • To develop a robust and reusable heterogeneous palladium catalyst for continuous-flow carbon-carbon coupling reactions.
  • To evaluate the performance of the developed catalyst in benchmark Mizoroki-Heck and Suzuki-Miyaura reactions.
  • To assess the catalyst's versatility and stability over extended reaction periods.

Main Methods:

  • Immobilization of a bis(diphenylphosphinoethyl)amine-palladium complex onto Merrifield resin to create the Pd-SCORPI heterogeneous catalyst.
  • Testing the catalyst in continuous-flow Mizoroki-Heck reactions using 4-iodoanisole and n-butyl acrylate.
  • Evaluating the catalyst in a continuous-flow Suzuki-Miyaura protocol with 4'-iodoacetophenone and phenylboronic acid.
  • Analyzing substrate scope for various aryl halides and alkenes.

Main Results:

  • Pd-SCORPI demonstrated high stability and efficiency in continuous-flow Mizoroki-Heck reactions, achieving a turnover number (TON) of 1115 and over 92% conversion for 14 days.
  • The catalyst exhibited versatility, effectively coupling aryl halides with electron-donating and electron-withdrawing groups with diverse alkenes.
  • In Suzuki-Miyaura flow reactions, Pd-SCORPI yielded 91% isolated product, with a TON of 1242 and stable operation for 150 hours.

Conclusions:

  • The developed Pd-SCORPI catalyst is a durable and highly efficient heterogeneous system for continuous-flow carbon-carbon coupling.
  • Its stability, recyclability, and broad substrate scope highlight its potential for advancing green chemistry.
  • Pd-SCORPI offers a promising platform for sustainable and scalable industrial chemical processes.