Immobilization of Cinchona Quaternary Ammonium Salts as the Chiral Phase Transfer Catalysts on Multi-walled Carbon Nanotubes and Their Application in Enantioselective Alkylation

doi:10.3724/SP.J.1088.2012.11213

Abstract

Abstract: The pyrene-tagged cinchona quaternary ammonium salt, the chiral phase transfer catalysts (PTC-1), was synthesized and immobilized on multi-walled carbon nanotubes (MWCNTs). The new catalysts (PTC-1/MWCNTs) were employed in enantioselective alkylation of N-(diphenylmethyene)glycine tert-butyl ester. UV-Vis absorption spectra show the effect of different organic solvents on the adsorption and desorption of PTC-1 onto and from MWCNTs, respectively. The results show that 5.3 mg PTC-1 can be loaded on 10 mg MWCNTs in toluene, and 0.02025 mg PTC-1 was desorbed from 12.7 mg PTC-1/MWCNTs when washed by CHCl₃. In the enantioselective alkylation of different halohydrocarbons with N-(diphenylmethyene)glycine tert-butyl ester using PTC-1/MWCNTs as a catalyst, the alkylating products were obtained with high yield and ee value. Furthermore, PTC-1/MWCNTs catalyst can be recovered and used repeatedly. PTC-1/MWCNTs as a new catalyst is effective in enantioselective alkylation of multiple halohydrocarbon.

Key words: multi-walled carbon nanotube, chiral phase transfer catalyst, cinchona alkaloid, adsorption, enantioselective alkylation

LIU Jian, LIU , SHI Xin, YANG Qi-Hua. Immobilization of Cinchona Quaternary Ammonium Salts as the Chiral Phase Transfer Catalysts on Multi-walled Carbon Nanotubes and Their Application in Enantioselective Alkylation[J]. Chinese Journal of Catalysis, 2012, 33(5): 891-897.

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