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Synthesis and enantioselectivities of soluble polymers incorporating optically active binaphthyl and binaphthol
Author(s) -
Zou Xiaowei,
Zhang Shuwei,
Cheng Yixiang,
Liu Yan,
Huang Hui,
Wang Chunyan
Publication year - 2007
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.26523
Subject(s) - benzaldehyde , monomer , polymerization , polymer , polymer chemistry , fourier transform infrared spectroscopy , chemistry , catalysis , materials science , organic chemistry , chemical engineering , engineering
A polymer ( P‐1 ) was synthesized through the polymerization of ( S )‐6,6′‐dibromo‐3,3′‐dibutyl‐1,1′‐binaphthol with ( S )‐2,2′‐dioctoxy‐1,1′‐binaphthyl‐6,6′‐boronic acid in a Pd‐catalyzed Suzuki reaction, and another polymer ( P‐2 ) was synthesized through the polymerization of ( S )‐6,6′‐dibromo‐3,3′‐dibutyl‐1,1′‐binaphthol with ( S )‐6,6′‐diethynyl‐2,2′‐dioctoxy‐1,1′‐binaphthyl in a Pd‐catalyzed Sonogashira reaction. The two polymers showed good solubility in some common solvents and were characterized with NMR, Fourier transform infrared, gel permeation chromatography, and circular dichroism spectroscopy. The application of the chiral monomers and polymers in the asymmetric addition of diethyl zinc to benzaldehyde was studied. The results indicated that P‐1 , P‐2 , and the monomer ( S )‐3,3′‐dibutyl‐1,1′‐binaphthol were efficient ligands in the asymmetric addition of diethyl zinc to benzaldehyde. The chiral polymer ligands P‐1 and P‐2 were more efficient than their monomeric version, ( S )‐3,3′‐dibutyl‐1,1′‐binaphthol, and could be easily recovered and reused without a loss of catalytic activity or enantioselectivity. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007