Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase

Research output: Contribution to journalArticleScientificpeer-review

Researchers

Research units

  • University of Helsinki
  • Johannes Gutenberg University Mainz
  • Università Degli Studi di Trieste
  • University of Oulu

Abstract

HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon–carbon bond formation between electron-rich (hetero)aryls with O2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the competing nature of acid-catalyzed and radical cationic ODHs, and indicate that both mechanisms operate with the current material.

Details

Original languageEnglish
JournalChemistry - A European Journal
Publication statusPublished - 1 Jan 2019
MoE publication typeA1 Journal article-refereed

    Research areas

  • carbon nanotubes, C−C coupling, heterogeneous catalysis, oxidative dehydrogenative coupling

ID: 36963231