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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
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 - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402087
Subject(s) - hypervalent molecule , chemistry , oxidizing agent , reagent , iodine , nitro , benzene , ligand (biochemistry) , redox , medicinal chemistry , functional group , combinatorial chemistry , organic chemistry , alkyl , biochemistry , receptor , polymer
A practical approach for the oxidation of unactivated C sp3 H bonds by an ortho ‐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 tert ‐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.