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

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

Tao Wang ^a,c, ,
Yuan Lyu ^a ,
Kai Xiong ^d ,
Wenlong Wang ^a ,
Hao Zhang ^e ,
Zhuangping Zhan ^d ,
Zheng Jiang ^e ,
Yunjie Ding ^a,b

a. Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b. State Key Laboratory of catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
c. University of Chinese Academy of Sciences, Beijing 100049, China;
d. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China;
e. Shanghai Synchrotron Radiation Facility, Shanghai Institute of Applied Physics, Chinese Academy of Sciences, Shanghai 201204, China

Received Date: 22 February 2017
Revised Date: 23 March 2017

Fund Project: This work was supported by the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB17020400).

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.
- (S)-4,4’-divinyl-BINAP,
- (S)-5,5’-divinyl-BINAP,
- Porous organic polymers supported,
- ruthenium,
- Heterogeneous asymmetric
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