π-Allylic Sulfonylation in Water with Amphiphilic Resin-Supported Palladium-Phosphine Complexes

Abstract

π-Allylic substitution of allyl esters with sodium arylsulfinate was performed with an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported phosphine-palladium complex in water as a single reaction medium under heterogeneous conditions to give allyl sulfones in good to high yields. Catalytic asymmetric allylic substitution of cycloalkenyl esters also took place in water using a PS-PEG resin-supported chiral imidazo­indolephosphine-palladium complex to give cycloalkenyl sulfones with up to 81% ee.

Key words

π-allylpalladium - sulfone - aqueous media - polymer support - palladium catalyst

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One preliminary example (Table [1] , entry 5) has been reported in reference 7b.

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Purchased from Rapp Polymere GmbH, Tübingen, Germany.