Tetrahedron p. 6657 - 6670 (1999)
Update date:2022-08-03
Topics:
Sollewijn Gelpke, Arjan E.
Veerman, Johan J.N.
Goedheijt, Marcel Schreuder
Kamer, Paul C.J.
Van Leeuwen, Piet W.N.M.
Hiemstra, Henk
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.
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(1999)