New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

S. M.Humayun Kabir, Mami Miura, Shigeru Sasaki, Genta Harada, Yoshiyuki Kuwatani, Masato Yoshida, Masahiko Iyoda

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.

Original languageEnglish
Pages (from-to)761-774
Number of pages14
JournalHeterocycles
Volume52
Issue number2
DOIs
Publication statusPublished - 2000 Feb 1
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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