Categories: C-I Bond Formation >
Synthesis of iodohydrins
Recent Literature
The reduction of IBX to IBA in the presence of molecular iodine in DMSO
generates hypoiodous acid (IOH), which reacts with various olefins as well as
α,β-unsaturated ketones leading to their respective iodohydrins with anti
stereochemistry. The same redox chemistry in acetonitrile containing TFA
produces iodonium ions for facile iodination of aromatic compounds.
J. N. Moorthy, K. Senapati, S. Kumar, J. Org. Chem., 2009,
74, 6287-6290.
The use of iodine and Oxone in acetic acid/acetic anhydride enables an
inexpensive, environmentally friendly, and highly efficient regio- and
diastereoselective iodoacetoxylation of alkenes and alkynes in a simple one-pot
process.
T. Hokamp, A. T. Storm, M. Yusubov, T. Wirth,
Synlett, 2018, 29, 415-418.
Acetyl hypoiodite (CH3CO2I) is readily generated in situ
by oxidation of molecular iodine by (diacetoxyiodo)benzene (DAIB) and can be
utilized for the synthesis of 1,2-iodo-cofunctionalized derivatives of alkenes.
Conversion of both atoms of molecular iodine to I+ results in 100%
iodine atom economy for the reported iodo-cofunctionalization of alkenes.
H. Gottam, T. K. Vinod, J. Org. Chem., 2011,
76, 974-977.
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.
Highly regioselective ring opening of epoxides to halohydrins has been
carried out in impressive yields with hydrogen and lithium halides in presence
of β-cyclodextrin using water as solvent.
M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron,
2002, 58, 6003-6008.
A β-boron effect accounts for high regioselectivity in electrophilic addition
reactions to allylic MIDA (N-methyliminodiacetic acid) boronates. The
boryl moiety is retained in the product when B(MIDA) is used as the nucleophilic
stabilizer.
Y. Li, W.-X. Fan, S. Luo, A. Tofimova, Y. Liu, J.-H. Xue, L. Yang, Q. Li, H.
Wang, A. K. Yudin, J. Am. Chem. Soc.,
2023, 145, 7548-7558.