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Alkyl Iodide Initiators for Organocatalyzed Living Radical Polymerization
No.185(December 2020)
Living radical polymerization can control molecular weight far better than conventional radical polymerization, but it requires a toxic transition-metal catalyst, which remains in the product. To solve this problem, Goto et al. reported that alkyl iodides (1-4) can act as efficient initiators for organocatalyzed living radical polymerization.1-3) Metal-free, low polydisperse polymers could be obtained by this method utilizing monomers with an appropriate alkyl iodide and an organocatalyst such as BMPI and BNI (Figures 1, 2). They also reported the polymerization method using azide anions as a catalyst and an azide source for one-pot synthesis of polymers with an azido group at the terminal,4) and green conditions using a bulk or green solvent;5) the use of these initiators is currently expanding.
Figure 1. The scheme of living radical polymerization.
Figure 2. The range of proper initiators and catalysts for each monomers
References
- 1) a) Systematic Study on Alkyl Iodide Initiators in Living Radical Polymerization with Organic Catalysts
- b) A. Goto, T. Fukuda, Y. Tsujii, US 7399814, 2008.
- c) A. Goto, PCT Int. Appl. WO 2015122404, 2015.
- 2) Reversible Generation of a Carbon-Centered Radical from Alkyl Iodide Using Organic Salts and Their Application as Organic Catalysts in Living Radical Polymerization
- 3) Photocontrolled Organocatalyzed Living Radical Polymerization Feasible over a Wide Range of Wavelengths
- 4) Solvent-Selective Reactions of Alkyl Iodide with Sodium Azide for Radical Generation and Azide Substitution and Their Application to One-Pot Synthesis of Chain-End-Functionalized Polymers
- 5) Biocompatible Choline Iodide Catalysts for Green Living Radical Polymerization of Functional Polymers
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