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Sulfobutyl Ether‐β‐Cyclodextrins: Promising Supramolecular Carriers for Aqueous Organometallic Catalysis
Author(s) -
Blach Philippe,
Landy David,
Fourmentin Sophie,
Surpateanu Gheorghe,
Bricout Hervé,
Ponchel Anne,
Hapiot Frédéric,
Monflier Eric
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505051
Subject(s) - chemistry , supramolecular chemistry , cyclodextrin , catalysis , aqueous solution , ether , triphenylphosphine , supramolecular catalysis , phosphine , combinatorial chemistry , substrate (aquarium) , organic chemistry , molecule , oceanography , geology
The potentialities of sulfobutyl ether‐β‐CDs derivatives as supramolecular carrier in a biphasic Tsuji–Trost reaction catalyzed by a water‐soluble palladium complex of trisulfonated triphenylphosphine have been investigated. The efficiency of these cyclodextrins (CDs) strongly depends on the average molar substitution degree of cyclodextrin and the highest rate enhancements were obtained with cyclodextrins containing about 7 sulfobutyl ether groups. This result was attributed to the absence of a strong interaction between this cyclodextrin and the trisulfonated triphenylphosphine used to dissolve the catalyst in the aqueous phase and to the presence of an extended hydrophobic cavity allowing a better molecular recognition between the substrate and the cyclodextrin. This constitutes the first example of a non‐interacting β‐cyclodextrin/phosphine couple with high catalytic activities.