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 Citations (Scopus)

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

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Indium
cross coupling
Cross Reactions
Palladium
Iodides
iodides
halides
reagents
indium
palladium
Calcium Gluconate
synthesis
Bromides
Dimers
bromides
dimers
Electrons
matrices
electrons

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals. / Lehmann, Ute; Awasthi, Smita; Minehan, Thomas.

In: Organic Letters, Vol. 5, No. 14, 10.07.2003, p. 2405-2408.

Research output: Contribution to journalArticle

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