On the origin of cine -substitution in the Stille coupling of trisubstituted iodoalkene and trans -vinylstannane

Naoki Kanoh, Yutaro Ohno, Tomohiro Itagaki, Hayato Fukuda, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Factors determining the course of reaction (i.e., usual coupling vs. abnormal cine-substitution) in the Stille coupling of trisubstituted iodoalkene and trans-vinylstannane were investigated. The palladium-catalyzed reaction with triphenylarsine and lithium chloride in N-methylpyrrolidone gave the normal Stille coupling product in good yield and good selectivity, while the use of N,N-diisopropylethylamine and cuprous iodide in toluene afforded the cine-substituted product exclusively. It is proposed that transmetalation between vinylpalladium and vinylstannane species determines the course of reaction.

Original languageEnglish
Article numberST-2013-U0685-L
Pages (from-to)2660-2664
Number of pages5
JournalSynlett
Volume24
Issue number20
DOIs
Publication statusPublished - 2013 Dec 17

Keywords

  • Stille reaction
  • alkenes
  • cross-coupling
  • palladium
  • regioselectivity

ASJC Scopus subject areas

  • Organic Chemistry

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