Highly selective oxidative cross‐coupling polymerization with copper(I)‐bisoxazoline catalysts

Abstract

Abstract The asymmetric oxidative coupling polymerization of methyl 6,6′‐dihydroxy‐2,2′‐binaphthalene‐7‐carboxylate with the copper‐diamine catalysts under an O 2 atmosphere was carried out. As is the case with the CuCl‐2,2′‐( S )‐isopropylidenbis(4‐phenyl‐2‐oxazoline) [( S )IPhO] catalyst, a polymer with a high cross‐coupling selectivity of 96% was obtained in 71% yield, whose THF‐soluble part had a number‐average molecular weight of 4.5 × 10 3 . To estimate the enantioselectivity with respect to the cross‐coupling linkage in the obtained polymer, the model asymmetric oxidative cross‐coupling reaction with CuCl‐( S )IPhO was also conducted, and the products showed a 94% cross‐coupling selectivity and enantioselectivity of 31% ee ( S ). © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 6287–6294, 2005