Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals

Ute Lehmann, Smita Awasthi, Thomas Minehan

Research output: Contribution to journalArticle

77 Scopus citations

Abstract

(Matrix presented) Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl 2Pd(PPh3)2 to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.

Original languageEnglish (US)
Pages (from-to)2405-2408
Number of pages4
JournalOrganic Letters
Volume5
Issue number14
DOIs
StatePublished - Jul 10 2003
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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