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  Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor

Hsu, W.-h., Reischauer, S., Seeberger, P. H., Pieber, B., & Cambié, D. (2022). Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor. Beilstein Journal of Organic Chemistry, 18, 1123-1130. doi:10.3762/bjoc.18.115.

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 Creators:
Hsu, Wei-hsin1, Author           
Reischauer, Susanne2, Author           
Seeberger, Peter H.3, Author           
Pieber, Bartholomäus2, Author                 
Cambié, Dario1, Author                 
Affiliations:
1Dario Cambié, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_3256668              
2Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2522692              
3Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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Free keywords: flow chemistry; heterogeneous catalysis; metallaphotoredox catalysis; packed bed; photochemistry
 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 present in the reaction mixture are the substrate and a base. The metallaphotoredox cross-coupling of sulfinates with aryl halides was used as a model system. 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.

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Language(s): eng - English
 Dates: 2022-08-292022
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
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 Identifiers: DOI: 10.3762/bjoc.18.115
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Title: Beilstein Journal of Organic Chemistry
  Abbreviation : Beilstein J. Org. Chem.
Source Genre: Journal
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Publ. Info: Frankfurt, Germany : Beilstein-Institut
Pages: - Volume / Issue: 18 Sequence Number: - Start / End Page: 1123 - 1130 Identifier: ISSN: 1860-5397