Photoredox catalyzed hydroazolylation of alkenes via phosphoranyl radicals

Herein, a general protocol for the hydroazolylation of alkenes with N-hydroxyl azoles is reported. These reactions proceed via a phosphoranyl radical that is accessed by photoredox catalysis, followed by radical coupling of the resulting azole radical to the alkene radical. The key point of this rea...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-05, Vol.11 (10), p.2839-2844
Main Authors: Zhu, Fan, Qiao, Zhi, He, Na, Nong, Chunxiao, He, Qiping, Meilan Xi, Song, Xizhong, Lin, Jun, Chen, Jingbo, Jin, Yi
Format: Article
Language:English
Subjects:
Alkenes
Azoles
Catalysis
Catalysts
Conjugation
Heterocyclic compounds
Nitrogen atoms
Phosphine
Phosphines
Photoredox catalysis
Substrates
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Summary:Herein, a general protocol for the hydroazolylation of alkenes with N-hydroxyl azoles is reported. These reactions proceed via a phosphoranyl radical that is accessed by photoredox catalysis, followed by radical coupling of the resulting azole radical to the alkene radical. The key point of this reaction lies in the specific binding between the hydroxy group on N-hydroxyazole and alkyl phosphine. This specificity enables the reaction to overcome the selectivity issues associated with the existing hydroazolylation reactions, arising from the conjugation effects of different nitrogen atoms in azole substrates, leading to N1/N2/N3 reaction site selectivity problems. Moreover, this protocol is also applicable to both intramolecular alkenes and external non-terminal alkenes.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo00233d