Asian Journal of Organic Chemistry
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Managing Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang
Impact Factor: 2.292
ISI Journal Citation Reports © Ranking: 2013: 27/58 (Chemistry Organic)
Online ISSN: 2193-5815
June 04, 2014
VIP: A Practical Approach for the Oxidation of Unactivated Csp3–H Bonds with o-Nitro-DIB as Efficient Hypervalent Iodine(III) Reagent
Shin A. Moteki, Sermadurai Selvakumar, Tiexin Zhang, Asuka Usui, and Keiji Maruoka*
The practical site-selective oxidation of unactivated Csp3–H bonds was achieved by using an ortho-nitrophenyl-substituted hypervalent iodine(III) reagent. The characteristic feature of the reagent is that the ortho-nitro group coordinates to the adjacent iodine center through a dipolar interaction, which induces the single substitution of the acetoxy ligand by tert-butyl hydroperoxide. As a result, a bulky, electrophilic iodanyl radical is generated, which can efficiently activate the inert Csp3–H bonds in a highly site-specific manner. The reagent is stable towards moisture, and the preparation of the reagent is simple and straightforward, which permits the use of this reagent for semipreparatory scale reactions.
Received June 13, 2014, published online July 02, 2014, DOI: 10.1002/ajoc.201402087 – read now.
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