Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis

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Abstract: An unprecedented enantioselective protonation reaction enabled by photoredox catalytic radical coupling is developed. Under cooperative dicynopyrazine‐derived chromophore (DPZ) as a photosensitizer and a chiral phosphoric acid catalyst, and Hantzsch ester as a sacrificial reductant, the transformations between α‐substituted enones and cyanoazaarenes or 2‐(chloromethyl) azaaren‐1‐iums can proceed a tandem reduction, radical coupling, and enantioselective protonation process efficiently. Two classes of pharmaceutically important enantioenriched azaarene variants, which contain a synthetically versatile ketone‐substituted tertiary carbon stereocenter at the β‐ or γ‐position of the azaarenes, are synthesized with high yields and ees.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis ; day:17 ; month:01 ; year:2024 ; extent:9
Advanced science ; (17.01.2024) (gesamt 9)

Creator
Kong, Manman
Wang, Zhuoxi
Ban, Xu
Zhao, Xiaowei
Yin, Yanli
Zhang, Junmin
Jiang, Zhiyong

DOI
10.1002/advs.202307773
URN
urn:nbn:de:101:1-2024011814023761688003
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:28 AM CEST

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Associated

  • Kong, Manman
  • Wang, Zhuoxi
  • Ban, Xu
  • Zhao, Xiaowei
  • Yin, Yanli
  • Zhang, Junmin
  • Jiang, Zhiyong

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