Functionalized arylzinc compounds in ethereal solvent: Direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides

Ryo Ikegami, Akiko Koresawa, Takanori Shibata, Kentaro Takagi

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Arylzinc compounds, ArZnX, were conveniently prepared in high yields by the reaction of zinc powder with aryl iodides, which contain electron-withdrawing groups such as CO2CH3, CN, Br, or CF3 at the ortho-, meta- or para-position, or electron-donating groups such as CH3, OCH3, or H, at 70 °C in THF, at 100 °C, or at 130 °C in diglyme, respectively. Pd(dba)2 exhibited an outstanding efficient catalytic effect for the cross-coupling of these ethereal solutions of ArZnX with allylic halides to afford a variety of functionalized allylbenzenes in high yields; the reactions were mostly carried out at 0 °C for 5-30 min in the presence of 5 mol % of catalyst. The conversion of the aryl iodides to allylbenzenes via two reactions could be accomplished in one pot.

Original languageEnglish
Pages (from-to)2195-2199
Number of pages5
JournalJournal of Organic Chemistry
Volume68
Issue number6
DOIs
Publication statusPublished - 2003 Mar 21
Externally publishedYes

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Iodides
Powders
Electrons
Zinc
Catalysts
zinc iodide
allylbenzene
diglyme

ASJC Scopus subject areas

  • Organic Chemistry

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Functionalized arylzinc compounds in ethereal solvent : Direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides. / Ikegami, Ryo; Koresawa, Akiko; Shibata, Takanori; Takagi, Kentaro.

In: Journal of Organic Chemistry, Vol. 68, No. 6, 21.03.2003, p. 2195-2199.

Research output: Contribution to journalArticle

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