1355078-53-3Relevant articles and documents
High performance of N -alkoxycarbonyl-imines in triethylborane-mediated tin-free radical addition
Yamada, Ken-Ichi,Konishi, Takehito,Nakano, Mayu,Fujii, Shintaro,Cadou, Romain,Yamamoto, Yasutomo,Tomioka, Kiyoshi
experimental part, p. 1547 - 1553 (2012/03/26)
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.
