Novel synthesis of a new skeletal compound benzonaphthazepine by regioselective C-H activation utilizing the intramolecular coordination of an amine to Pd

Takashi Harayama, Tomonori Sato, Akihiro Hori, Hitoshi Abe, Yasuo Takeuchi

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The novel synthesis of a new skeletal compound, benzonaphthazepine, from N-bromobenzylnaphthylamine using a Pd reagent is described. In the biaryl coupling reaction of N-bromobenzylnaphthylamine using a Pd reagent, the intramolecular coordination of the benzylamino group to Pd causes regioselective C-H activation at the peri position relative to the amine group on the naphthalene ring, producing benzonaphthazepine in good to excellent yield. The bulkiness of the substituent at C7 on the naphthalene ring affects the regioselectivity of the biaryl coupling reaction.

Original languageEnglish
Pages (from-to)1446-1456
Number of pages11
JournalSynthesis
Issue number9
Publication statusPublished - Jun 18 2004

    Fingerprint

Keywords

  • C-H activation
  • Coordination
  • Heterocycles
  • Palladium
  • Regioselectivity

ASJC Scopus subject areas

  • Organic Chemistry

Cite this