Molecules 2010, 15(4), 2857-2871; doi:10.3390/molecules15042857
Article

Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol

Department of Physical and Organic Chemistry, “Jožef Stefan” Institute, Jamova cesta 39, 1000 Ljubljana, Slovenia
* Author to whom correspondence should be addressed.
Received: 7 January 2010; in revised form: 24 February 2010 / Accepted: 19 March 2010 / Published: 20 April 2010
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Abstract: Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hydrogen peroxide for the oxidation of hydrochloric acid to molecular chlorine. Aryliodine(III) dichlorides were formed in 72–91% isolated yields in the reaction of aryl iodides with 30% aqueous hydrogen peroxide and hydrochloric acid at ambient temperature. A study of the effect that substituents on the aromatic ring have on the formation and stability of aryliodine(III) dichlorides shows that the transformation is easier to achieve in the presence of the electron-donating groups (i.e. methoxy), but in this case the products rapidly decompose under the reported reaction conditions to form chlorinated arenes. The results suggest that oxidation of hydrogen chloride with hydrogen peroxide is the initial reaction step, while direct oxidation of aryl iodide with hydrogen peroxide is less likely to occur.
Keywords: oxidative halogenation; hydrogen peroxide; fluorinated alcohol; hypervalent iodine halides; chlorination

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MDPI and ACS Style

Podgoršek, A.; Iskra, J. Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol. Molecules 2010, 15, 2857-2871.

AMA Style

Podgoršek A, Iskra J. Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol. Molecules. 2010; 15(4):2857-2871.

Chicago/Turabian Style

Podgoršek, Ajda; Iskra, Jernej. 2010. "Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol." Molecules 15, no. 4: 2857-2871.

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