Cu-Catalyzed Electrochemical Activation of Nitromethane\nto Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction

Here,\nwe report an electrochemical approach to generate an aldoxime-substituted\nnitrile oxide via the activation of nitromethane. The Cu-catalyzed\nHuisgen reaction of this 1,3-dipole with alkynes enables successful\npreparation of 48 new isoxazole aldoximes, which are typically challenging\nto synthesize by other methods, in 52 to 97% yields with excellent\nregioselectivity and chemoselectivity in a single step. Moreover,\n20 3,3′-bisisoxazoles are prepared from the isoxazole aldoxime\nproducts in good yields via a two-step sequence.

Publication Details

Journal
Figshare
Published
2024-12-10
DOI
https://doi.org/10.1021/acs.orglett.4c04146.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Cu-Catalyzed Electrochemical Activation of Nitromethane\nto Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction

Figshare
Radical Photochemical Reactions
article

Cu-Catalyzed Electrochemical Activation of Nitromethane\nto Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction

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Abstract

Here,\nwe report an electrochemical approach to generate an aldoxime-substituted\nnitrile oxide via the activation of nitromethane. The Cu-catalyzed\nHuisgen reaction of this 1,3-dipole with alkynes enables successful\npreparation of 48 new isoxazole aldoximes, which are typically challenging\nto synthesize by other methods, in 52 to 97% yields with excellent\nregioselectivity and chemoselectivity in a single step. Moreover,\n20 3,3′-bisisoxazoles are prepared from the isoxazole aldoxime\nproducts in good yields via a two-step sequence.

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Radical Photochemical Reactions
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Cu-Catalyzed Electrochemical Activation of Nitromethane\nto Access Aldoxime-Substituted Nitrile Oxide for Huisgen Reaction · Figshare (2024) | TGRS Research Map | TGRS