Section 50
Chapter 49,849

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

Lehmann, U.; Awasthi, S.; Minehan, T.

Organic Letters 5(14): 2405-2408


ISSN/ISBN: 1523-7060
PMID: 12841741
DOI: 10.1021/ol0345428
Accession: 049848080

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[reaction: see text] 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(2)Pd(PPh(3))(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.

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