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Postsynthetic Metalation of a Robust Hydrogen-Bonded Organic Framework for Heterogeneous Catalysis

Han, Bin, Wang, Hailong, Wang, Chiming, Wu, Hui, Zhou, Wei, Chen, Banglin, Jiang, Jianzhuang
Journal of the American Chemical Society 2019 v.141 no.22 pp. 8737-8740
Suzuki reaction, acetates, aromatic hydrocarbons, catalysts, catalytic activity, crystallization, hydrogen bonding, palladium, surface area, triazines
Hydrogen-bonded organic framework (HOF)-based catalysts still remain unreported thus far due to their relatively weak stability. In the present work, a robust porous HOF (HOF-19) with a Brunauer–Emmett–Teller surface area of 685 m² g–¹ was reticulated from a cagelike building block, amino-substituted bis(tetraoxacalix[2]arene[2]triazine), depending on the hydrogen bonding with the help of π–π interactions. The postsynthetic metalation of HOF-19 with palladium acetate afforded a palladium(II)-containing heterogeneous catalyst with porous hydrogen-bonded structure retained, which exhibits excellent catalytic performance for the Suzuki–Miyaura coupling reaction with the high isolation yields (96–98%), prominent stability, and good selectivity. More importantly, by simple recrystallization, the catalytic activity of deactivated species can be recovered from the isolation yield 46% to 92% for 4-bromobenzonitrile conversion at the same conditions, revealing the great application potentials of HOF-based catalysts.