Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes

Wen-Wei Lin, Florian Ilgen, Paul Knochel

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The described polyfunctional arylmagnesium reagents, resulting from the highly regioselective addition of magnesium phenylselenide to functionalized arynes, can be trapped by a range of electrophiles, yielding polyfunctional selenoethers in 45-85% yields. Furthermore, these Grignard reagents can be used in Negishi cross-coupling reactions with iodoarenes after transmetalation to the corresponding arylzinc compounds, furnishing functionalized biaryl products in 55-73% yields.

Original languageEnglish
Pages (from-to)1941-1944
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number12
DOIs
Publication statusPublished - 2006 Mar 20

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Magnesium
Cross Reactions

Keywords

  • Aryne
  • Organomagnesium reagent
  • Selenoether

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Preparation of highly functionalized arylmagnesium reagents by the addition of magnesium phenylselenide to arynes. / Lin, Wen-Wei; Ilgen, Florian; Knochel, Paul.

In: Tetrahedron Letters, Vol. 47, No. 12, 20.03.2006, p. 1941-1944.

Research output: Contribution to journalArticle

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