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  Dichloromethylation of enones by carbon nitride photocatalysis

Mazzanti, S., Kurpil, B., Pieber, B., Antonietti, M., & Savateev, A. (2020). Dichloromethylation of enones by carbon nitride photocatalysis. Nature Communications, 11: 1387. doi:10.1038/s41467-020-15131-0.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-EB75-F Version Permalink: http://hdl.handle.net/21.11116/0000-0005-EB76-E
Genre: Journal Article

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 Creators:
Mazzanti, Stefano1, Author              
Kurpil, Bogdan1, Author              
Pieber, Bartholomäus2, Author              
Antonietti, Markus3, Author              
Savateev, Aleksandr1, Author              
Affiliations:
1Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2421702              
2Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2522692              
3Markus Antonietti, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863321              

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Free keywords: Synthetic chemistry methodology; Photocatalysis
 Abstract: Small organic radicals are ubiquitous intermediates in photocatalysis and are used in organic synthesis to install functional groups and to tune electronic properties and pharmacokinetic parameters of the final molecule. Development of new methods to generate small organic radicals with added functionality can further extend the utility of photocatalysis for synthetic needs. Herein, we present a method to generate dichloromethyl radicals from chloroform using a heterogeneous potassium poly(heptazine imide) (K-PHI) photocatalyst under visible light irradiation for C1-extension of the enone backbone. The method is applied on 15 enones, with γ,γ-dichloroketones yields of 18–89%. Due to negative zeta-potential (−40 mV) and small particle size (100 nm) K-PHI suspension is used in quasi-homogeneous flow-photoreactor increasing the productivity by 19 times compared to the batch approach. The resulting γ,γ-dichloroketones, are used as bifunctional building blocks to access value-added organic compounds such as substituted furans and pyrroles.

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Language(s): eng - English
 Dates: 2020-03-132020
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1038/s41467-020-15131-0
Other: Mazzanti2020
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Title: Nature Communications
  Abbreviation : Nat. Commun.
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 11 Sequence Number: 1387 Start / End Page: - Identifier: ISSN: 2041-1723