Phosphonium salts based on 2H-imidazole: synthesis by direct C–H functionalization of imidazole N-oxides

A convenient approach towards previously unknown phosphonium salts containing a non-aromatic 2 H -imidazole moiety is reported. The approach is based on a direct nucleophilic C(sp 2 )-H functionalization of 2 H -imidazole 1-oxides with triphenylphosphine acting as a nucleophile. Herewith, the hetero...

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Published inRussian chemical bulletin Vol. 72; no. 11; pp. 2693 - 2697
Main Authors Akulov, A. A., Pershin, A. A., Deleva, A. A., Varaksin, M. V., Charushin, V. N., Chupakhin, O. N.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.11.2023
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Imidazole
Inorganic Chemistry
Nucleophiles
Organic Chemistry
Synthesis
oxides
phosphonium salts
nucleophilic substitution of hydrogen (S
)
nitrones
C-H functionalization
imidazoles
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Summary:A convenient approach towards previously unknown phosphonium salts containing a non-aromatic 2 H -imidazole moiety is reported. The approach is based on a direct nucleophilic C(sp 2 )-H functionalization of 2 H -imidazole 1-oxides with triphenylphosphine acting as a nucleophile. Herewith, the heterocyclic N -oxide moiety is utilized as an auxiliary group contributing to an abstraction of C-H proton during the elimination process. Newly obtained compounds can be a subject of further modification, e.g. used for the synthesis of monodeuterated 2 H -imidazoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-4074-9