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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.


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.