Biphasic Aqueous Organometallic Catalysis Promoted by Cyclodextrins: How to Design the Water‐Soluble Phenylphosphane to Avoid Interaction with Cyclodextrin - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2008

Biphasic Aqueous Organometallic Catalysis Promoted by Cyclodextrins: How to Design the Water‐Soluble Phenylphosphane to Avoid Interaction with Cyclodextrin

Résumé

The ability of cyclodextrin to interactwithmeta-trisulfonated triphenylphosphane deriva-tives bearing one or two methyl (or methoxy)groups on the aromatic ring has been investigatedby NMR and UV-vis spectroscopy. In the case ofnativeb-cyclodextrin (b-CD), the presence of onemethyl or methoxy group in theortho-position oneach aromatic ring is necessary to hamper the for-mation of an inclusion complex between theb-CDandmeta-trisulfonated triphenylphosphane deriva-tives. In the case of methylatedb-CD, the formationof an inclusion complex is only observed when themeta-trisulfonated triphenylphosphane contains amethyl group in thepara-position. The poor affinityof methylatedb-CD towards modified trisulfonatedtriphenylphosphanes was attributed to the sterichindrance generated by the methyl groups on theCD secondary face. The absence or presence of aninteraction between phosphanes and methylatedb-CD was also confirmed by catalytic experiments.Thus, the phosphanes that do not interact with themethylated CD were the most efficient mass-trans-fer promoters in an aqueous biphasic palladium-cat-alyzed Tsuji–Trost reaction.

Dates et versions

hal-01667852 , version 1 (19-12-2017)

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Citer

Michel Ferreira, Hervé Bricout, Adlane Sayede, Anne Ponchel, Sophie Fourmentin, et al.. Biphasic Aqueous Organometallic Catalysis Promoted by Cyclodextrins: How to Design the Water‐Soluble Phenylphosphane to Avoid Interaction with Cyclodextrin. Advanced Synthesis and Catalysis, 2008, 350 (4), pp.609-618. ⟨10.1002/adsc.200700582⟩. ⟨hal-01667852⟩
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