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

Research output: Contribution to journalArticle

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.

LanguageEnglish
Pages4740-4747
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number34
DOIs
Publication statusPublished - 2018 Sep 16

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Alkynes
alkynes
musculoskeletal system
nitrogen atoms
Nitrogen
retarding
Ligands
catalysts
Atoms
ligands
Catalysts
Substrates
synthesis
Experiments
N-propargyl

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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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.",
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AU - Inoue, Daisuke

AU - Takaki, Asahi

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

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