8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts

Mamoru Ito, Daisuke Inoue, Asahi Takaki, Stephen Kyalo Kanyiva, Takanori Shibata

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Abstract

The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.

Original languageEnglish
Pages (from-to)4740-4747
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number34
DOIs
Publication statusPublished - 2018 Sep 16

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Keywords

  • Carbene ligands
  • Dibenzodiazocine
  • Gold
  • Homogeneous catalysis
  • Hydroarylation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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