Categories: C-I Bond Formation >
Synthesis of 1,2-iodoamines
Recent Literature
An efficient and mild thiophenol-promoted ring-opening of aziridines or epoxides
with iodine afforded β-iodo amines or β-iodo alcohols in very good yields.
J. Wu, X. Sun, W. Sun, S. Ye, Synlett, 2006,
2489-2491.
Aziridines are opened regioselectively with hydrogen and lithium halides to
yield β-haloamines in the presence of β-cyclodextrin using water as the solvent.
N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004,
501-502.
A catalyst- and metal-free visible-light-mediated protocol enables the
iodoamination of miscellaneous olefins in high yields under environmentally
benign reaction conditions using DMC as green and biodegradable solvent.
Furthermore, the protocol allows for late-stage functionalization of bioactive
molecules and can be scaled to gram quantities of product.
S. Engl, O. Reiser, Org. Lett., 2021, 23,
5581-5586.
Related
The combination of sodium periodate, potassium iodide, and sodium azide is an
efficient, simple, and inexpensive reagent system for azidoiodination of
alkenes. The regiospecific 1,2-azidoiodination proceeds in an anti-Markovnikov
fashion to produce β-iodoazides in excellent yields.
P. V. Chouthaiwale, P. U. Karabal, G. Suryavanshi, A. Sudalai, Synthesis, 2010,
3879-3882.