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  • Title: High performance of N-alkoxycarbonyl-imines in triethylborane-mediated tin-free radical addition.
    Author: Yamada K, Konishi T, Nakano M, Fujii S, Cadou R, Yamamoto Y, Tomioka K.
    Journal: J Org Chem; 2012 Feb 03; 77(3):1547-53. PubMed ID: 22208724.
    Abstract:
    Triethylborane-mediated tin-free radical alkylation of N-alkoxycarbonyl-imines, such as N-Boc-, N-Cbz-, and N-Teoc-imines, proceeded smoothly at a low temperature (-78 to -20 °C) to give the corresponding adducts in high yield. Although the formation of isocyanate was the major unfavorable reaction at room temperature, a one-pot conversion of N-Boc-imine to N-ethoxycarbonyl-adduct was possible through the corresponding isocyanate generated in situ. The higher performance of N-alkoxycarbonyl-imine than those of N-Ts- and N-PMP-imines is rationalized by a moderate electron-withdrawing character of an alkoxycarbonyl group that makes both addition of alkyl radical and trapping of the resulting aminyl radical by triethylborane efficiently fast.
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