Unusual thiophilic ring-opening of fused oligothiophenes with organolithium reagents

Konstantin Chernichenko, Nikolai Emelyanov, Ilya Gridnev, Valentine G. Nenajdenko

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Organolithium reagents attack the sulfur atoms of fused oligothiophenes producing ring-opened organolithium intermediates that can be trapped with a suitable electrophile. The reaction was found to be general for fused thieno[2,3-b]-thiophenes and some [3,2-b]-fused oligothiophenes. Thermodynamic (organilithiums basicity) and mechanistic (RLi coordination by neighboring sulfur) aspects control the substrate scope and regioselectivity of the reaction. When competitive deprotonation of the substrate is possible, high selectivity toward ring-opening was observed with n-BuLi when compared with the other tested organolithiums. The recently discovered octathio[8]circulene produces multifold ring-opening products.

Original languageEnglish
Pages (from-to)6812-6818
Number of pages7
JournalTetrahedron
Volume67
Issue number36
DOIs
Publication statusPublished - 2011 Sep 9
Externally publishedYes

Keywords

  • Oligothiophene
  • Organolithium
  • Ring-opening
  • Thiophene
  • Thiophilic

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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