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Catalysis of C–C Cross‐Coupling Reactions in Aqueous Solvent by Bis‐ and Tris(ferrocenyltriazolylmethyl)arene–β‐Cyclodextrin‐Stabilized Pd 0 Nanoparticles
Author(s) -
Liang Liyuan,
Diallo Abdou K.,
Salmon Lionel,
Ruiz Jaime,
Astruc Didier
Publication year - 2012
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201200098
Subject(s) - chemistry , catalysis , tris , cyclodextrin , adduct , heck reaction , nanoparticle , quinoxaline , solvent , aqueous solution , medicinal chemistry , coupling reaction , suzuki reaction , green chemistry , organic chemistry , palladium , combinatorial chemistry , polymer chemistry , reaction mechanism , nanotechnology , biochemistry , materials science
Mono‐, bis‐, and tris(4‐ferrocenyl‐1,2,3‐triazolylmethyl)arene–β‐cyclodextrin adducts have been used to prepare new Pd 0 nanoparticle (PdNP) catalysts for C–C cross‐coupling reactions in EtOH/H 2 O. The results show that these catalysts work well in Miyaura–Suzuki and Heck reactions with iodoarenes at 25 and 80 °C, respectively, with turnover numbers (TONs) of up to 31000 for standard Miyaura–Suzuki reactions of PhI when 10 ppm of the Pd catalyst (5 nm PdNPs) were used. The results show the benefit for PdNP catalysis of encapsulating hydrophobic catalytic systems between peripheral water‐solubilizing cyclodextrins as bolamphiphile‐like materials because the open monoferrocenyltriazolylmethylbenzene system shows a considerably reduced catalytic efficiency compared with bis‐ and tris(4‐ferrocenyl‐1,2,3‐triazolylmethyl)arene–β‐cyclodextrin adducts.