Dearomative Intramolecular Diels–Alder/Sulfur Extrusion Reaction of Thiophenes with Alkynes Using peri-Substituted Naphthalene as a Tether

Takashi Okitsu*, Yoshiki Shinohara, Haoran Luo, Manabu Hatano, Takayuki Yakura*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Dearomative intramolecular Diels–Alder/sulfur extrusion reaction of thiophenes with alkynes successfully afforded fluoranthenes in moderate to excellent yields. The proximity of both reactive sites fixed at the peri-position of naphthalene would play an important role in the progress of this reaction. Tri(o-tolyl)phosphine effectively suppressed the side reactions as a sulfur scavenger.

Original languageEnglish
Article numbere202301031
JournalChemistry - An Asian Journal
Volume19
Issue number4
DOIs
StatePublished - 2024/02/16

Keywords

  • alkyne
  • dearomatization
  • Diels–Alder
  • fluoranthene
  • thiophene

ASJC Scopus subject areas

  • Biochemistry
  • General Chemistry
  • Organic Chemistry

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