Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2010-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/4/2857/ |
| _version_ | 1819043256009228288 |
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| author | Ajda Podgoršek Jernej Iskra |
| author_facet | Ajda Podgoršek Jernej Iskra |
| author_sort | Ajda Podgoršek |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-21T09:53:53Z |
| format | Article |
| id | doaj.art-a85ecc60c1fd4e298a243e635ff8d79d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T09:53:53Z |
| publishDate | 2010-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a85ecc60c1fd4e298a243e635ff8d79d2022-12-21T19:08:07ZengMDPI AGMolecules1420-30492010-04-011542857287110.3390/molecules15042857Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated AlcoholAjda PodgoršekJernej IskraOxidative 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.http://www.mdpi.com/1420-3049/15/4/2857/oxidative halogenationhydrogen peroxidefluorinated alcoholhypervalent iodine halideschlorination |
| spellingShingle | Ajda Podgoršek Jernej Iskra Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol Molecules oxidative halogenation hydrogen peroxide fluorinated alcohol hypervalent iodine halides chlorination |
| title | Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol |
| title_full | Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol |
| title_fullStr | Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol |
| title_full_unstemmed | Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol |
| title_short | Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol |
| title_sort | conversion of aryl iodides into aryliodine iii dichlorides by an oxidative halogenation strategy using 30 aqueous hydrogen peroxide in fluorinated alcohol |
| topic | oxidative halogenation hydrogen peroxide fluorinated alcohol hypervalent iodine halides chlorination |
| url | http://www.mdpi.com/1420-3049/15/4/2857/ |
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