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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

2012; Wiley; Volume: 2012; Issue: 17 Linguagem: Inglês

10.1002/ejic.201200098

1099-0682

Liyuan Liang, Abdou K. Diallo, Lionel Salmon, Jaimé Ruiz, Didier Astruc,

Click Chemistry and Applications

Abstract 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.