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DOI: 10.1055/s-0028-1083557
π-Allylic Sulfonylation in Water with PS-PEG Pd-Phosphine Complexes
Contributor(s):Yasuhiro Uozumi, Toshimasa SuzukaInstitute for Molecular Science, Okazaki, Japan
π-Allylic Sulfonylation in Water with Amphiphilic Resin-Supported Palladium-Phosphine Complexes
Synthesis 2008, 1960-1964
Publication History
Publication Date:
20 November 2008 (online)
Key words
allylic substitution - palladium - asymmetric synthesis - sulfones
Significance
Amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported phosphine-palladium complexes were found to be effective catalysts for π-allylic sulfonylation in water. Thus, PS-PEG resin-supported phosphine-palladium complex 1 was prepared according to the reported procedures (Tetrahedron Lett. 1997, 38, 3557). π-Allyic sulfonylation of 1,3-diphenyl-2-propenyl acetate 3 with PhSO2Na in water was carried out with catalyst 1 to give 1,3-diphenyl-1-phenylsulfonyl-2-propene in 90% yield. The catalyst 1 was recovered and reused three times without any loss of catalytic activity (average 88% yield).
Comment
Previously, the author developed a PS-PEG resin-supported chiral imidazoindolephosphine-palladium complex 2 for the asymmetric π-allylic substitution in water (e.g., J. Am. Chem. Soc. 2001, 123, 2919). Asymmetric π-allylic sulfonylation of cycloalkenyl esters was catalyzed in water with the polymeric chiral complex 2 to give the corresponding cycloalkenyl sulfones 6a-c in good yield with 33-81% ee.