Dichloromethylation of enones by carbon nitride photocatalysis

Stefano Mazzanti, Bogdan Kurpil, Bartholomäus Pieber, Markus Antonietti and Aleksandr Savateev ()
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Stefano Mazzanti: Max Planck Institute of Colloids and Interfaces
Bogdan Kurpil: Max Planck Institute of Colloids and Interfaces
Bartholomäus Pieber: Max Planck Institute of Colloids and Interfaces
Markus Antonietti: Max Planck Institute of Colloids and Interfaces
Aleksandr Savateev: Max Planck Institute of Colloids and Interfaces

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-15131-0

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