Heterogeneous metallaphotoredox catalysis in a continuous-flow packed bed reactor

  1. Wei-Hsin Hsu,
  2. Susanne ReischauerORCID Logo,
  3. Peter H SeebergerORCID Logo,
  4. Bartholomäus Pieber and
  5. Dario CambiéORCID Logo

Submitting author affiliation: MPI Potsdam, Potsdam, Germany

Beilstein Arch. 2022, 202256. https://doi.org/10.3762/bxiv.2022.56.v1

Published 29 Jun 2022

  • Preprint

Abstract

Metallaphotoredox catalysis is a powerful and versatile synthetic platform that enables cross-couplings under mild conditions without the need for noble metals. Its growing adoption in drug discovery has translated into an increased interest in sustainable and scalable reaction conditions. Here, we report a continuous flow approach to metallaphotoredox catalysis using a heterogeneous catalyst that combines the function of a photo- and a nickel catalyst in a single material. The catalyst is embedded in a packed bed reactor to combine reaction and (catalyst) separation in one step. The use of a packed bed simplifies the translation of optimized batch reaction conditions to continuous flow, as the only components presents in the reaction mixture are the substrate and a base. Using the cross-coupling of sulfinates with aryl halides as a model system, a productivity of 4 mmol/h was achieved. The catalyst was shown to be stable, with a very low decrease of the yield (~1% per day) during a continuous experiment over seven days, and to be effective for C–O arylations when carboxylic acids are used as nucleophile instead of sulfinates.

Keywords: Metallaphotoredox catalysis; flow chemistry; packed bed; heterogeneous catalysis, photochemistry

Supporting Information

Format: DOCX Size: 7.4 MB   Download
Format: PDF Size: 45.7 KB   Download
Format: PDF Size: 45.4 KB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Hsu, W.-H.; Reischauer, S.; Seeberger, P. H.; Pieber, B.; Cambié, D. Beilstein Arch. 2022, 202256. doi:10.3762/bxiv.2022.56.v1

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2022 Hsu et al.; licensee Beilstein-Institut.
This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia