Jump to main content
Jump to site search

Issue 19, 2017
Previous Article Next Article

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

Author affiliations

Abstract

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(sp2)–C(sp2) 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′-dibromo-1,1′-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.

Graphical abstract: Reconnaissance of reactivity of an Ag(ii)SO4 one-electron oxidizer towards naphthalene derivatives

Back to tab navigation

Supplementary files

Article information


Submitted
27 Jun 2017
Accepted
15 Aug 2017
First published
30 Aug 2017

New J. Chem., 2017,41, 10742-10749
Article type
Paper

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

A. K. Budniak, M. Masny, K. Prezelj, M. Grzeszkiewicz, J. Gawraczyński, Ł. Dobrzycki, M. K. Cyrański, W. Koźmiński, Z. Mazej, K. J. Fijałkowski, W. Grochala and P. J. Leszczyński, New J. Chem., 2017, 41, 10742
DOI: 10.1039/C7NJ02299A

Social activity

Search articles by author

Spotlight

Advertisements