Carbohydrate Polymers p. 200 - 210 (2018)
Update date:2022-08-03
Topics: Suzuki-Miyaura coupling Arylboronic Acids Water Aryl Halides Picolinamide β-Cyclodextrin Supramolecular catalyst
Luo, Kaixiu
Zhang, Lu
Yang, Rui
Jin, Yi
Lin, Jun
Novel supramolecular catalysts for Suzuki-Miyaura coupling were prepared and characterized by NMR, FT-IR, TEM, XRD, TGA, and XPS. The resulting picolinamide-modified β-cyclodextrin/Pd(II) complex (Pd(II)@PCA-β-CD) showed very efficient catalytic activity for Suzuki-Miyaura coupling of aryl, benzyl, and allyl halides with arylboronic acids in an environmentally benign aqueous solution. Various organic halides including chlorides can produce good to excellent yields with phenyl-boronic acid and a catalytic amount of Pd(II)@PCA-β-CD. This hydro-soluble catalyst was capable of being reused for at least eight runs with only a slight loss of catalytic activity. A putative mechanism of the Pd(II)/Pd(IV) catalytic cycle was also explored and calculated by ab initio QM/MM methods.
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