Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis

doi:10.1016/S1872-2067(17)62826-2

Abstract

Abstract:

Two vinyl-functionalized chiral 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl (BINAP) ligands, (S)-4,4’-divinyl-BINAP and (S)-5,5’-divinyl-BINAP, were successfully synthesized. Chiral BINAP-based porous organic polymers (POPs), denoted as 4-BINAP@POPs and 5-BINAP@POPs, were efficiently prepared via the copolymerization of vinyl-functionalized BINAP with divinyl benzene under solvothermal conditions. Thorough characterization using nuclear magnetic resonance spectroscopy, thermogravimetric analysis, extended X-ray absorption fine structure analysis, and high-angle annular dark-field scanning transmission electron microscopy, we confirmed that chiral BINAP groups were successfully incorporated into the structure of the materials considered to contain hierarchical pores. Ru was introduced as a catalytic species into the POPs using different synthetic routes. Systematic investigation of the resultant chiral Ru/POP catalysts for heterogeneous asymmetric hydrogenation of β-keto esters revealed their excellent chiral inducibility as well as high activity and stability. Our work thereby paves a path towards the use of advanced hierarchical porous polymers as solid chiral platforms for heterogeneous asymmetric catalysis.

Key words: (S)-4,4’-divinyl-BINAP, (S)-5,5’-divinyl-BINAP, Porous organic polymers supported, ruthenium, Heterogeneous asymmetric, hydrogenation, β-keto esters

Tao Wang, Yuan Lyu, Kai Xiong, Wenlong Wang, Hao Zhang, Zhuangping Zhan, Zheng Jiang, Yunjie Ding. Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis[J]. Chinese Journal of Catalysis, 2017, 38(5): 890-898.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62826-2

https://www.cjcatal.com/EN/Y2017/V38/I5/890

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