Catalytic [2 + 2 + 2] cycloaddition of benzothiophene dioxides with α,ω-diynes for the synthesis of condensed polycyclic compounds

Yu Ki Tahara, Manami Gake, Riku Matsubara, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A Rh-catalyzed intermolecular [2 + 2 + 2] cycloaddition of the 2,3-double bond of benzothiophene dioxides with α,ω-diynes gave sulfone-containing cycloadducts in high yields. This is the first example of a catalytic [2 + 2 + 2] cycloaddition that uses the 2,3-double bond of a heterole as an ene moiety. The consecutive reaction of benzodithiophene tetraoxide with 2,3-naphthylene-tethered 1,7-diyne gave an 11-ring condensed polycyclic compound in one pot.

Original languageEnglish
Pages (from-to)5980-5983
Number of pages4
JournalOrganic Letters
Volume16
Issue number22
DOIs
Publication statusPublished - 2014 Nov 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Catalytic [2 + 2 + 2] cycloaddition of benzothiophene dioxides with α,ω-diynes for the synthesis of condensed polycyclic compounds'. Together they form a unique fingerprint.

Cite this