A Practical Approach for the Oxidation of Unactivated Csp3H Bonds with o‐Nitro(diacetoxyiodo)benzene as an Efficient Hypervalent Iodine(III)‐Based Oxidizing Agent. Issue 9 (2nd July 2014)

• Record Type: Journal Article
• Authors: Moteki, Shin A.; Selvakumar, Sermadurai; Zhang, Tiexin; Usui, Asuka; Maruoka, Keiji
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 9(2014:Sep.)
• Page Start: 932
• Page End: 935
• Publication Date: 2014-07-02
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201402087
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A practical approach for the oxidation of unactivated C_sp3H bonds by an <italic>ortho</italic>‐nitrophenyl‐substituted hypervalent iodine(III) reagent is presented. The nitro group coordinates to the adjacent iodine center through dipolar interaction, which leads to a single substitution of the acetate ligand by <italic>tert</italic>‐butyl hydroperoxide. As a result, a strong iodanyl radical is formed, which can activate the inert C_sp3H bonds in a highly efficient manner. The reagent is stable in the presence of moisture, and can be used for oxidation reactions on semipreparative scale.</p> </abstract>