Comparison of oxidative aromatic coupling and the scholl reaction

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  • Instytut Chemii Bioorganicznej Polskiej Akademii Nauk
  • Warsaw University of Technology
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Translated title of the contributionOxidative aromatische Kupplung und Scholl-Reaktion im Vergleich
Original languageEnglish
Pages (from-to)9900-9930
Number of pages31
JournalAngewandte Chemie
Volume52
Issue number38
Publication statusPublished - 14 Jul 2013

Abstract

Does the dehydrogenative coupling of aromatic compounds mediated by AlCl3 at high temperatures and also by FeCl3, MoCl 5, PIFA, or K3[Fe(CN)6] at room temperature proceed by the same mechanism in all cases? With the growing importance of the synthesis of aromatic compounds by double CH activation to give various biaryl structures, this question becomes pressing. Since some of these reactions proceed only in the presence of non-oxidizing Lewis acids and some only in the presence of certain oxidants, the authors venture the hypothesis that, depending on the electronic structure of the substrates and the nature of the "catalyst", two different mechanisms can operate. One involves the intermediacy of a radical cation and the other the formation of a sigma complex between the acid and the substrate. The goal of this Review is to encourage further mechanistic studies hopefully leading to an in-depth understanding of this phenomenon. Where is the oxidant? Although the coupling of arenes in the presence of Lewis acids has been known for some time, the differentiation between reactions in the presence of a non-oxidizing Lewis acid (Scholl reaction) and in the presence of an oxidizing Lewis acid has been lost over the years. This Review highlights the similarities and differences between these reactions, which most probably proceed by two different mechanisms.

Keywords

    arene coupling, biaryls, Lewis acids, oxidative coupling, Scholl reaction

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Cite this

Comparison of oxidative aromatic coupling and the scholl reaction. / Grzybowski, Marek; Skonieczny, Kamil; Butenschön, Holger et al.
In: Angewandte Chemie , Vol. 52, No. 38, 14.07.2013, p. 9900-9930.

Research output: Contribution to journalReview articleResearchpeer review

Grzybowski M, Skonieczny K, Butenschön H, Gryko DT. Comparison of oxidative aromatic coupling and the scholl reaction. Angewandte Chemie . 2013 Jul 14;52(38):9900-9930. doi: 10.1002/anie.201210238, 10.1002/ange.201210238
Grzybowski, Marek ; Skonieczny, Kamil ; Butenschön, Holger et al. / Comparison of oxidative aromatic coupling and the scholl reaction. In: Angewandte Chemie . 2013 ; Vol. 52, No. 38. pp. 9900-9930.
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