Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives

被引:14
作者
Budniak, Adam K. [1 ,2 ]
Masny, Michal [3 ]
Prezelj, Kristina [1 ]
Grzeszkiewicz, Mikolaj [4 ]
Gawraczynski, Jakub [1 ,2 ]
Dobrzycki, Lukasz [5 ]
Cyranski, Michal K. [5 ]
Kozminski, Wiktor [2 ]
Mazej, Zoran [6 ]
Fijalkowski, Karol J. [1 ]
Grochala, Wojciech [1 ]
Leszczynski, Piotr J. [1 ]
机构
[1] Univ Warsaw, Ctr New Technol, Zwirki & Wigury 93, PL-02089 Warsaw, Poland
[2] Univ Warsaw, Fac Chem, Pasteur 1, PL-02093 Warsaw, Poland
[3] Univ Warsaw, Fac Phys, Pasteur 5, PL-02093 Warsaw, Poland
[4] Warsaw Univ Technol, Dept Mat Engn, Woloska 141, PL-02507 Warsaw, Poland
[5] Univ Warsaw, Fac Chem, Czochralski Lab Adv Crystal Engn, Zwirki & Wigury 101, PL-02089 Warsaw, Poland
[6] Jozef Stefan Inst, Dept Inorgan Chem & Technol, Jamova Cesta 39, Ljubljana 1000, Slovenia
关键词
2-NAPHTHOL DERIVATIVES; RADICAL-CATION; AMINE COMPLEX; ARENES; FLUORINATION; SUBSTITUTION; LIGANDS; ULLMANN; DEHYDRODIMERIZATION; OXIDATION;
D O I
10.1039/c7nj02299a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We test divalent silver sulphate, Ag(II)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp(2))-C(sp(2)) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F. . .I), leading to 4,4'-disubstituted-1,1'-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2'-, 2,7'-, and 7,7'-dibromo1,1'-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5'-disubstituted-1,1'-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C-C coupling methods, and it preserves them, if present. Ag(II)SO4 may be easily electrochemically regenerated from the Ag(I)HSO4 byproduct. However, the C-C coupling method currently suffers from low yields, up to 17%, and it requires further optimization.
引用
收藏
页码:10742 / 10749
页数:8
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