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Highly regio- and stereo-selective copolymerization of CO2 with racemic propylene oxide catalyzed by unsymmetrical (S,S,S)-salenCo(III) complexes

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  • Special Topic Advances in Principles of Polymerization
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Abstract

A novel unsymmetrical (S,S,S)-salen ligand bearing a derived chiral-BINOL was synthesized by the reaction of the condensation product of (1S,2S)-1,2-diaminocyclohexane mono(hydrogen chloride) with 3-adamanyl-5-tert-butyl-2-hydroxybenzaldehyde and 3-formoyl-2-hydroxy-2′-alkyloxy-1,1′-binaphthyl, which originated from (S)-1,1′-bi-2-naphthol via a four-step reaction. The cobalt complexes of this ligand, in conjunction with a nucleophilic cocatalyst, exhibited excellent activity in catalyzing asymmetric, regio- and stereo-selective copolymerization of CO2 and racemic propylene oxide. The highest record of kinetic resolution coefficient (K rel) was obtained with the use of binary catalyst system consisting of (S,S,S)-salenCo(III) complex 1c and bulky bis(triphenylphosphine)-iminium chloride (PPNCl). The resulting poly(propylene carbonate)s have more than 99% carbonate linkages and more than 98% head-to-tail content.

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, China

    WeiMin Ren, WenZhen Zhang & XiaoBing Lu

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  1. WeiMin Ren
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  2. WenZhen Zhang
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  3. XiaoBing Lu
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Correspondence to XiaoBing Lu.

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Ren, W., Zhang, W. & Lu, X. Highly regio- and stereo-selective copolymerization of CO2 with racemic propylene oxide catalyzed by unsymmetrical (S,S,S)-salenCo(III) complexes. Sci. China Chem. 53, 1646–1652 (2010). https://doi.org/10.1007/s11426-010-4049-1

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  • DOI: https://doi.org/10.1007/s11426-010-4049-1

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