Picolinamide modified β-cyclodextrin/Pd (II) complex: Asupramolecular catalyst for Suzuki-Miyaura coupling of aryl, benzyl and allyl halides with arylboronic acids in water

Kaixiu Luo; Lu Zhang; Rui Yang; Yi Jin; Jun Lin

doi:10.1016/j.carbpol.2018.07.089

Picolinamide modified β-cyclodextrin/Pd (II) complex: Asupramolecular catalyst for Suzuki-Miyaura coupling of aryl, benzyl and allyl halides with arylboronic acids in water

Carbohydr Polym. 2018 Nov 15:200:200-210. doi: 10.1016/j.carbpol.2018.07.089. Epub 2018 Jul 30.

Authors

Kaixiu Luo¹, Lu Zhang¹, Rui Yang², Yi Jin³, Jun Lin⁴

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China.
² Faculty of Science, Kunming University of Science and Technology, Kunming, 650500, PR China. Electronic address: yangrui911@163.com.
³ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China. Electronic address: jinyi@ynu.edu.cn.
⁴ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China. Electronic address: linjun@ynu.edu.cn.

PMID: 30177158
DOI: 10.1016/j.carbpol.2018.07.089

Abstract

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.

Keywords: Catalyst; Coupling; Eco-friendly; Supramolecular; Suzuki-Miyaura; β-cyclodextrin /Pd (II) complex.