Palladium-catalyzed and hybrid acids-assisted synthesis of [60]fulleroazepines in one pot under mild conditions: Annulation of N-sulfonyl-2-aminobiaryls with [60]fullerene through sequential C-H bond activation, C-C and C-N bond formation

Venkatachalam Rajeshkumar, Fu Wei Chan, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

An extraordinarily efficient hybrid acids-assisted, palladium-catalyzed and chelating-group-assisted C-H bond activation of N-sulfonyl-2-aminobiaryls and their annulations with [60]fullerene via sequential C-C and C-N bond formation at room temperature to afford [60]fulleroazepines is demonstrated. The formation of [60]fulleroazepines is highly regioselective and tolerant to both electron-withdrawing and electron-donating groups on the aryl moiety and the reaction gives monofunctionalized fullerenes in good yields (up to 54% isolated yield and 92% based on converted C 60).

Original languageEnglish
Pages (from-to)2473-2483
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number13
DOIs
StatePublished - 17 Sep 2012

Keywords

  • C-C, C-N bond formation
  • C-H activation
  • fullerenes
  • hybrid acids
  • palladium

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