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Highly Selective Macrocycle Formations by Metathesis Catalysts Fixated in Nanopores

Cited 23 time in Web of Science Cited 24 time in Scopus
Authors
Jee, Joo-Eun; Cheong, Jian Liang; Lim, Jaehong; Chen, Cheng; Hong, Soon Hyeok; Lee, Su Seong
Issue Date
2013-02
Publisher
American Chemical Society
Citation
Journal of Organic Chemistry, Vol.78 No.7, pp. 3048-3056
Keywords
복합학
Abstract
Ruthenium-based metathesis catalysts immobilized on mesocellular siliceous foam (MCF) bearing large nanopores proved highly efficient and selective for macrocyclic ring-closing metathesis (RCM). Kinetic studies revealed that the homogeneous counterpart exhibited far higher activity that accounted for more oligomerization pathways and resulted in less macrocyclization products. Meanwhile, the immobilized catalysts showed lower conversion rates leading to higher yields of macrocyclic products in a given reaction time, with conversion rates and yields dependent upon pore size, catalyst loading density, and linker length. The macrocycle formations via RCM were accelerated by increasing the pore size and decreasing the catalyst loading density while retaining the comparably high yield. The catalysts immobilized on MCF, of which silica surface is rigid and pores are relatively large, showed high conversion rates and yields compared with an analogue immobilized on TentaGel resins, of which backbone becomes flexible upon swelling in the reaction medium. It is noteworthy that the selectivity for the macrocyclic RCM can be significantly improved by tuning the catalyst initiation rates via immobilization onto the support materials in which well-defined three-dimentional network of large nanopores are deployed.
ISSN
0022-3263
Language
English
URI
https://hdl.handle.net/10371/91674
DOI
https://doi.org/10.1021/jo302823w
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College of Natural Sciences (자연과학대학)Dept. of Chemistry (화학부)Journal Papers (저널논문_화학부)
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