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Iodobenzene Dichloride

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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 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.