Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to CN double bonds
作者:Fabien Cougnon、Laurence Feray、Samantha Bazin、Michèle P. Bertrand
DOI:10.1016/j.tet.2007.09.014
日期:2007.11
Diethylzinc-mediated radical addition to CNbonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of
The utility of N-sulfonylimines as radical acceptors was investigated under the different reaction conditions such as the stannyl radical-mediated addition reaction, the triethylborane-mediated tin-free radical reaction, and the zinc-mediated aqueous-medium radical reaction. The alkyl radical addition reaction of N-sulfonylimines proceeded effectively without the activation by Lewis acid. These reactions were successfully extended to one-pot reactions for preparing a wide range of amine derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
Miyabe, Hideto; Ueda, Masafumi; Naito, Takeaki, Chemical Communications, 2000, # 20, p. 2058 - 2060