Copper-Catalyzed Reaction of N-Monosubstituted Hydrazones with CBr4: Unexpected Fragmentation and Mechanistic Study-Reference-Cited by-同舟云学术

Copper-Catalyzed Reaction of N-Monosubstituted Hydrazones with CBr4: Unexpected Fragmentation and Mechanistic Study

Published:2023-08-09 Issue:8 Volume:13 Page:1194
ISSN:2073-4344
Container-title:Catalysts
language:en
Short-container-title:Catalysts

Author:

Nenajdenko Valentine G.¹^ORCID,Kazakova Anna A.²,Novikov Alexander S.³^ORCID,Shikhaliyev Namig G.⁴,Maharramov Abel M.⁴,Qajar Ayten M.⁴,Atakishiyeva Gulnar T.⁴,Niyazova Aytan A.⁵,Khrustalev Victor N.²⁶^ORCID,Shastin Alexey V.⁷,Tskhovrebov Alexander G.²^ORCID

Affiliation:

1. Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 Bld. 3, 119991 Moscow, Russia

2. Research Institute of Chemistry, Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia

3. Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab, 7/9, 199034 Saint Petersburg, Russia

4. Department of Organic Chemistry, Baku State University, Z. Xalilov 23, 1148 Baku, Azerbaijan

5. Department of Engineering and Applied Sciences, Azerbaijan State University of Economics, M. Mukhtarov 194, 1001 Baku, Azerbaijan

6. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, 119991 Moscow, Russia

7. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Russia

Abstract

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.

Funder

RUDN University Strategic Academic Leadership Program

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis,General Environmental Science

Link

https://www.mdpi.com/2073-4344/13/8/1194/pdf

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