Copper-Catalyzed Reaction of IN/I-Monosubstituted Hydrazones with CBr[sub.4]: Unexpected Fragmentation and Mechanistic Study

The copper catalyzed reaction of N-monosubstituted hydrazones with carbon tetrabromide leads to formation of expected dibromodiazadienes and unexpected dibromostyrenes. The experimental and theoretical study of the reaction revealed a key role of N-centered radicals, which can eliminate aryl radical...

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Bibliographic Details
Published in:Catalysts 2023-08, Vol.13 (8)
Main Authors: Nenajdenko, Valentine G, Kazakova, Anna A, Novikov, Alexander S, Shikhaliyev, Namig G, Maharramov, Abel M, Qajar, Ayten M, Atakishiyeva, Gulnar T, Niyazova, Aytan A, Khrustalev, Victor N, Shastin, Alexey V, Tskhovrebov, Alexander G
Format: Article
Language:English
Subjects:
Copper
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Summary:The copper catalyzed reaction of N-monosubstituted hydrazones with carbon tetrabromide leads to formation of expected dibromodiazadienes and unexpected dibromostyrenes. The experimental and theoretical study of the reaction revealed a key role of N-centered radicals, which can eliminate aryl radicals to form the corresponding dibromostyrenes. Alternatively, the oxidation of intermediate N-centered radicals by Cu(II) results in the corresponding diazadienes. These two reaction pathways are competitive directions of the reaction. Consequently, the reaction can be useful for the synthesis of both dibromostyrenes and rare dibromodiazadienes.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal13081194