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Arenesulfonyl iodides: The third universal class of functional initiators for the metal-catalyzed living radical polymerization of methacrylates and styrenes

Authors

  • Virgil Percec,

    Corresponding author
    1. Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
    • Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
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  • Cristian Grigoras

    1. Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
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Abstract

The metal-catalyzed living radical polymerization of methyl methacrylate and styrene initiated with freshly prepared p-toluenesulfonyl iodide (TsI) and catalyzed with CuX/2,2′-bipyridine (bpy), where X is Cl, Br, or I, and various self-regulated copper-based catalytic systems, such as copper/bpy, copper(I) oxide/bpy, copper(I) sulfide/bpy, copper(I) selenide/bpy, and copper(I) telluride/bpy, is reported. The exchange of C[BOND]I into C[BOND]Br and C[BOND]Cl takes place when the living radical polymerization of methyl methacrylate is catalyzed by copper(I) bromide/bpy and copper(I) chloride/bpy, respectively. Therefore, the use of the TsI initiator facilitates the synthesis, starting from a single initiator, of poly(methyl methacrylate) containing C[BOND]I, C[BOND]Br, and C[BOND]Cl chain ends. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 3920–3931, 2005

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