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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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| Published in: | Organic chemistry frontiers an international journal of organic chemistry 2024-05, Vol.11 (10), p.2839-2844 |
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| Main Authors: | , , , , , , , , , |
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| Language: | English |
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| container_end_page | 2844 |
| container_issue | 10 |
| container_start_page | 2839 |
| container_title | Organic chemistry frontiers an international journal of organic chemistry |
| container_volume | 11 |
| creator | Zhu, Fan Qiao, Zhi He, Na Nong, Chunxiao He, Qiping Meilan Xi Song, Xizhong Lin, Jun Chen, Jingbo Jin, Yi |
| description | 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. |
| doi_str_mv | 10.1039/d4qo00233d |
| format | article |
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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. 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| ispartof | Organic chemistry frontiers an international journal of organic chemistry, 2024-05, Vol.11 (10), p.2839-2844 |
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| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Alkenes Azoles Catalysis Catalysts Conjugation Heterocyclic compounds Nitrogen atoms Phosphine Phosphines Photoredox catalysis Substrates |
| title | Photoredox catalyzed hydroazolylation of alkenes via phosphoranyl radicals |
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