Visible light-induced C(sp3)-H azolation of ethers via radical-polar crossover

Reported herein is a photochemical strategy for C(sp(3))-H azolation of ethers via a hydrogen-atom transfer and radical-polar crossover process, offering efficient access to valuable N-alkylated azoles under visible-light irradiation. The protocol is metal-free and photocatalyst-free, and exhibits g...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 19; pp. 2669 - 2672
Main Authors Huang, Cheng, Qin, Yu-Shu, Wang, Chen-Lu, Xiao, Peng, Tang, Sheng, Liu, Hong-Jun, Wei, Zhenhong, Cai, Hu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 29.02.2024
Royal Society of Chemistry
Subjects
Alkylation
Chemistry
Chemistry, Multidisciplinary
Crossovers
Ethers
Heterocyclic compounds
Hydrogen atoms
Light irradiation
Physical Sciences
Science & Technology
Substrates
FUNCTIONALIZATION
AZOLES
AMINATION
ABSTRACTION
ACTIVATION
BONDS
N-ALKYLATION
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Summary:Reported herein is a photochemical strategy for C(sp(3))-H azolation of ethers via a hydrogen-atom transfer and radical-polar crossover process, offering efficient access to valuable N-alkylated azoles under visible-light irradiation. The protocol is metal-free and photocatalyst-free, and exhibits good to excellent yields and broad substrate scope with regard to azoles. EPR experiments provide evidence for the formation of intermediates formed in situ.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d3cc06210d