Cover Picture: 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 (Asian J. Org. Chem. 9/2014). Issue 9 (September 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: 901
• Page End: 901
• Publication Date: 2014-09
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201490018
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>The practical, site‐selective</bold> oxidation of unactivated C_sp3‐H bonds was achieved by the use of a stable <italic>ortho</italic>‐nitrophenyl‐substituted hypervalent iodine(III) reagent. In their Communication on <ext-link ext-link-type="doi" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">page 932 ff.</ext-link>, Keiji Maruoka and co‐workers show that the presence of the nitro group adjacent to the iodine center leads to a single substitution of an acetate ligand by tert‐butyl hydroperoxide. Hence, the generation of a strong iodanyl radical was achieved, which can activate inert C_sp3‐H bonds in a highly efficient manner. Also, the use of such a bulky reagent "tips the balance" in favor of oxidation at the C3 over the C4 position on substituted cyclohexane rings. Image credit: Asuka Usui.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh18r6b2j5" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>