52165-46-5Relevant academic research and scientific papers
Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins
Bakthavachalam, Ananthan,Chuang, Hui-Chun,Yan, Tu-Hsin
, p. 5884 - 5894 (2014)
Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.
Hypervalent iodine-mediated aziridination of alkenes: Mechanistic insights and requirements for catalysis
Richardson, Robert D.,Desaize, Magalie,Wirth, Thomas
, p. 6745 - 6754 (2008/03/14)
By detailed study of the possible side reactions in the previously reported aziridination of alkenes with N-aminoheterocycles mediated by hypervalent iodine reagents, the requirements to make this reaction catalytic in iodoarene have been determined. The reaction requires an oxidant that will oxidise iodoarenes but that does not oxidise alkenes, but it is possible that no such oxidant actually exists! A method in which the hypervalent iodine reagent can be recycled without the need for reisolation is possible. Further study into the mechanism of this reaction gives tentative evidence that the reaction proceeds through formation of an aminoiodane that reacts directly with the alkene, contrary to previous literature reports in which an acetoxyamine intermediate is suggested. The temperature effect of this reaction is remarkable.
