Iodobenzene Dichloride
Recent Literature
A highly efficient and mild procedure for the oxidation of different types of
alcohols uses TEMPO as catalyst, iodobenzene dichloride as stoichiometric
oxidant, and pyridine as base. Oxidation of 1,2-diols gives α-hydroxy ketones or
α-diketones depending on the amount of oxidant used. High yielding procedures
for the preparation of iodoarene dichlorides have been developed.
X.-F. Zhao, C. Zhang, Synthesis, 2007,
551-557.
X.-F. Zhao, C. Zhang, Synthesis, 2007,
551-557.
α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and
an activating catalyst. Acyclic diazocarbonyls reacted faster than cyclics, and
β-diketones were much faster to react than β-keto esters or β-diesters.
K. E. Coffrey, G. K. Murphy,
Synlett, 2015, 26, 1003-1007.
The use of (dichloroiodo)benzene enables a mild and rapid nucleophilic
chlorination of readily available secondary and tertiary alkyl phenyl sulfides.
Enantioenriched benzylic sulfides can be converted to their corresponding
inverted chlorides with high stereospecificity. The chlorination of
sulfa-Michael derived sulfides provides elimination-sensitive β-chloro carbonyl
and nitro compounds in good yields.
D. Canestrari, S. Lancianesi, E. Badiola, C. Strinna, H. Ibrahim, M. F. A. Adamo, Org. Lett.,
2017, 19, 918-921.
A hypervalent iodine reagent-based α-carbonyl dihalogenation of diazoacetate
derivatives with either iodobenzene dichloride or iodotoluene difluoride results
in gem-dichlorination or gem-difluorination products, respectively.
The reaction is catalyzed by either Lewis acid or Lewis base and proceeds
rapidly and chemoselectively to the desired gem-difunctionalized products
in very good yield.
J. Tao, R. Tran, G. K. Murphy, J. Am. Chem. Soc., 2013,
135, 16312-16315.
PhICl2 in wet DMF forms an efficient system for difunctionalization
of various alkenes to provide either regioselective chloroformyloxylated
products or α-chlorinated olefinic products, depending on the type of structure
of the original unsaturated starting material. The mechanism of the reaction is
proposed and discussed.
L. Liu, D. Zhang-Negrerie, Y. Du, K. Zhao, Org. Lett., 2014,
16, 436-439.
Aliphatic and aromatic ketones can be directly converted into their
corresponding α-chloroketone acetals in very good yields using iodobenzene
dichloride in ethylene glycol in the presence of 4 Å molecular sieves at room
temperature.
J. Yu, C. Zhang, Synthesis, 2009,
2324-2328.
Various aliphatic and aromatic aldehydes are converted into their corresponding
carbamoyl azides in very good yields in the presence of iodobenzene dichloride
and sodium azide in acetonitrile under nitrogen.
X.-Q. Li, X.-F. Zhao, C. Zhang, Synthesis, 2008,
2589-2593.