Synthesis, Structure of Zinc Complexes Containing Sulfonylated Binaphtholate Ligands and Their Catalytic Activities towards Ring-Opening Polymerization of Lactide and ε-Caprolactone

Authors

  • Shuangliu Zhou,

    Corresponding author
    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
    • Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China, Tel.: 0086-0553-3869310; Fax: 0086-0553-3883517
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  • Yongyao Jiang,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Tao Xie,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Zhanshuan Wu,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Linmin Zhou,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Wenjing Xu,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Lijun Zhang,

    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
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  • Shaowu Wang

    Corresponding author
    1. Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China
    • Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China, Tel.: 0086-0553-3869310; Fax: 0086-0553-3883517
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Abstract

Reaction of sulfonylated binaphthol [2-hydroxy-2′-tosyloxy-1,1-binaphthyl (1a, Ts-Binol) or 2-hydroxy-2′-(phenylsulfonyloxy)-1,1-binaphthyl (1b, Ps-Binol)] with 1 equiv. of ZnEt2 afforded zinc complexes [(Ts-Binol)ZnEt]2 (2a) and [(Ps-Binol)ZnEt]2 (2b). Further reaction of zinc complexes 2a and 2b with benzyl alcohol (BnOH) gave the zinc benzyloxide [(Ts-Binol)2Zn2(OBn)2]2 (3a) and [(Ps-Binol)2Zn2(OBn)2]2 (3b). Alternatively, the zinc benzyloxides 3a and 3b could also be obtained by reaction of compound 1a or 1b with Zn(OBn)2 (in situ reaction of ZnEt2 and BnOH). The complexes were fully characterized by elemental analyses and spectroscopic analyses, and complexes 2a, 2b and 3a were further characterized by single-crystal X-ray analyses. The catalytic activities of these zinc complexes towards ring-opening polymerization of ε-caprolactone and D,L-lactide were studied.

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