Porous Rh/BINAP polymers as efficient heterogeneous catalysts for asymmetric hydroformylation of styrene: Enhanced enantioselectivity realized by flexible chiral nanopockets

doi:10.1016/S1872-2067(17)62790-6

Chinese Journal of Catalysis ›› 2017, Vol. 38 ›› Issue (4): 691-698.DOI: 10.1016/S1872-2067(17)62790-6

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Porous Rh/BINAP polymers as efficient heterogeneous catalysts for asymmetric hydroformylation of styrene: Enhanced enantioselectivity realized by flexible chiral nanopockets

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

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

Received:2016-12-15 Revised:2017-01-15 Online:2017-04-18 Published:2017-04-12
Supported by:
This work was supported by the Strategic priority Research Program of the Chinese Academy of Sciences (XDB17020400).

Abstract

Abstract:

A new chiral monomer, (S)-5,5'-divinyl-BINAP, was successfully synthesized and embedded into two different porous organic polymers (Poly-1 and Poly-2). After loading a Rh species, the catalysts were applied for the heterogeneous asymmetric hydroformylation of styrene. Compared with the homogeneous BINAP analogue, the enantioselectivity of Rh/Poly-1 catalyst was drastically increased by approximately 70%. The improved enantioselectivity of the porous Rh/BINAP polymers was attributed to the presence of flexible chiral nanopockets resulting from the increased bulk of the R groups near the catalytic center.

Key words: Porous organic polymer, Heterogeneous catalysis, Asymmetric hydroformylation, Enhanced enatioselectivity, Chiral nanopocket

Tao Wang, Wenlong Wang, Yuan Lü, Kai Xiong, Cunyao Li, Hao Zhang, Zhuangping Zhan, Zheng Jiang, Yunjie Ding. Porous Rh/BINAP polymers as efficient heterogeneous catalysts for asymmetric hydroformylation of styrene: Enhanced enantioselectivity realized by flexible chiral nanopockets[J]. Chinese Journal of Catalysis, 2017, 38(4): 691-698.

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Porous Rh/BINAP polymers as efficient heterogeneous catalysts for asymmetric hydroformylation of styrene: Enhanced enantioselectivity realized by flexible chiral nanopockets

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