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Fluorous Surface‐Active Distannoxane Catalysts
Author(s) -
Orita Akihiro,
Tanabe Shoko,
Ono Tatsuhiko,
Otera Junzo
Publication year - 2010
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.201000130
Subject(s) - chemistry , catalysis , reagent , solvent , aldol reaction , toluene , organic synthesis , substrate (aquarium) , organic solvent , organic chemistry , phase (matter) , dilution , combinatorial chemistry , chemical engineering , oceanography , physics , engineering , thermodynamics , geology
Fluorous distannoxanes (XR f 2 SnOSnR f 2 X) 2 ⋅n H 2 O ( R f =C 6 F 13 C 2 H 4 ) ( 1 : X=C 8 F 17 SO 3 , n =10; 4 : X=Cl, n =0) ( 1 ) catalyze the Mukaiyama aldol reaction and the allylation of aldehydes with tetraallyltin at room temperature in fluorous/organic biphasic solvent systems, in which the reactions proceed more rapidly than in a single organic or fluorous solvent. Due to the unique surface activity of 1 , the catalyst, organic substrate(s), and reagent(s) are distributed in both organic and fluorous phases to facilitate smooth reactions. Upon dilution with toluene after the reaction, the catalyst concentrates to the fluorous phase, while the organic substances migrate to the organic phase to effect facile catalyst recovery and recycling. By virtue of such a unique solvophilicity, a new version of fluorous biphase technology has been developed.