2-Iodo-<i>N</i>-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

DOI PDF Web Site 被引用文献3件 参考文献66件

書誌事項

公開日
2018-04-30
資源種別
journal article
権利情報
  • http://creativecommons.org/licenses/by/4.0
  • http://creativecommons.org/licenses/by/4.0
  • http://creativecommons.org/licenses/by/4.0
DOI
  • 10.3762/bjoc.14.82
公開者
Beilstein Institut

説明

<jats:p>Several <jats:italic>N</jats:italic>-isopropyliodobenzamides were evaluated as catalysts for the oxidation of benzhydrol to benzophenone in the presence of Oxone<jats:sup>®</jats:sup> (2KHSO<jats:sub>5</jats:sub>·KHSO<jats:sub>4</jats:sub>·K<jats:sub>2</jats:sub>SO<jats:sub>4</jats:sub>) as a co-oxidant at room temperature. A study on the substituent effect of the benzene ring of <jats:italic>N</jats:italic>-isopropyl-2-iodobenzamide on the oxidation revealed that its reactivity increased in the following order of substitution: 5-NO<jats:sub>2</jats:sub> < 5-CO<jats:sub>2</jats:sub>Me, 3-OMe < 5-OAc < 5-Cl < H, 4-OMe < 5-Me < 5-OMe. The oxidation of various benzylic and aliphatic alcohols using a catalytic amount of the most reactive 5-methoxy derivative successfully resulted in moderate to excellent yields of the corresponding carbonyl compounds. The high reactivity of the 5-methoxy derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols.</jats:p>

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