Synthesis and use of water-soluble sulfonated dibenzofuran-based phosphine ligands

The syntheses of three triphenylphosphine analogues with one, two or three phenyl groups replaced by 2-dibenzofuranyl groups, respectively, and one enantiopure analogue of the atropisomeric diphosphine MeO-BIPHEP with all four phenyl groups replaced by 2-dibenzofuranyl are reported. Sulfonation of t...

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Bibliographic Details
Published in:Tetrahedron 1999-05, Vol.55 (21), p.6657-6670
Main Authors: Sollewijn Gelpke, Arjan E., Veerman, Johan J.N., Schreuder Goedheijt, Marcel, Kamer, Paul C.J., van Leeuwen, Piet W.N.M., Hiemstra, Henk
Format: Article
Language:English
Subjects:
Heck reaction
Hydroformylation
Phosphines
Solvents and solvent effects
Suzuki reaction
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Summary:The syntheses of three triphenylphosphine analogues with one, two or three phenyl groups replaced by 2-dibenzofuranyl groups, respectively, and one enantiopure analogue of the atropisomeric diphosphine MeO-BIPHEP with all four phenyl groups replaced by 2-dibenzofuranyl are reported. Sulfonation of these compounds with sulfuric acid at rt proceeded with complete regioselectivity at the 8-position in the dibenzofuran moieties. These results proved the usefulness of dibenzofuran as a structural moiety in the synthesis of water-soluble phosphine ligands. The dibenzofuran-based, water-soluble triphenylphosphine analogues were used as ligands in palladium-catalysed aqueous phase Heck and Suzuki reactions and in the rhodium-catalysed two-phase hydroformylation of propene. A number of dibenzofuran-based phosphine ligands were synthesised. Sulfonation to obtain water-soluble analogues occurred under mild conditions and exclusively at the 8-position of the dibenzofuran skeleton. The ligands were tested in aqueous Heck and Suzuki reactions.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00312-9