Metal‐free Nucleophilic α‐Azidation of α‐Halohydroxamates with Azidotrimethylsilane

A mild and metal‐free synthetic method for α‐azido carbonyl derivatives via the nucleophilic α‐azidation of α‐halohydroxamates have been established. The reactions of trimethylsilyl azide with various α‐mono‐ and disubstituted azaoxyallyl cations, generated in situ from α‐halohydroxamates, afforded...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-12, Vol.10 (12), p.3257-3260
Main Authors: Lee, Chang Yoon, Kim, Sung‐Gon
Format: Article
Language:English
Subjects:
Azaoxyallyl cation
Azidation
Azidotrimethylsilane
Carbonyls
Organic azide
Organic chemistry
α-Azido carbonyl
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Summary:A mild and metal‐free synthetic method for α‐azido carbonyl derivatives via the nucleophilic α‐azidation of α‐halohydroxamates have been established. The reactions of trimethylsilyl azide with various α‐mono‐ and disubstituted azaoxyallyl cations, generated in situ from α‐halohydroxamates, afforded a wide range of hindered mono‐ and dialkyl α‐azido carbonyl derivatives in good yields in the presence of tetrabutylammonium fluoride as a catalyst. Sterically hindered α‐azido carbonyls: Mild and efficient synthetic method of α‐azido carbonyl derivatives has been established using the nucleophilic α‐azidation of α‐halohydroxamates. The reaction of TMSN3 with various α‐mono‐ and disubstituted α‐halohydroxamates using TBAF as a catalyst produced a wide range of hindered α‐azido carbonyl derivatives in good yields.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100556