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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)

Cover Picture: A Practical Approach for the Oxidation of Unactivated Csp3H Bonds with... The practical, site‐selective oxidation of unactivated Csp3‐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 Csp3‐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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

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)

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Publisher
Wiley
Copyright
Copyright © 2014 Wiley Subscription Services, Inc., A Wiley Company
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201490018
Publisher site
See Article on Publisher Site

Abstract

The practical, site‐selective oxidation of unactivated Csp3‐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 Csp3‐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.

Journal

Asian Journal of Organic Chemistry – Wiley

Published: Sep 1, 2014

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