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Cover Picture: A Practical Approach for the Oxidation of Unactivated C sp3 H Bonds with o ‐Nitro(diacetoxyiodo)benzene as an Efficient Hypervalent Iodine(III)‐Based Oxidizing Agent (Asian J. Org. Chem. 9/2014)
Author(s) -
Moteki Shin A.,
Selvakumar Sermadurai,
Zhang Tiexin,
Usui Asuka,
Maruoka Keiji
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201490018
Subject(s) - chemistry , hypervalent molecule , cyclohexane , oxidizing agent , reagent , iodine , nitro , benzene , redox , ligand (biochemistry) , medicinal chemistry , photochemistry , organic chemistry , alkyl , biochemistry , receptor
The practical, site‐selective oxidation of unactivated C sp3 ‐H bonds was achieved by the use of a stable ortho ‐nitrophenyl‐substituted hypervalent iodine(III) reagent. In their Communication on page 932 ff. , 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.