Categories: C-I Bond Formation >
Synthesis of 1,2-iodoamines
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.
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.