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Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

Ayumi Watanabe, Kazunori Miyamoto*, Tomohide Okada, Tomotake Asawa, Masanobu Uchiyama*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Bunkyo-ku 113-0033, Japan, Email: kmiyamol.f.u-tokyo.ac.jp, uchiyamamol.f.u-tokyo.ac.jp

A. Watanabe, K. Miyamoto, T. Okada, T. Asawa, M. Uchiyama, J. Org. Chem., 2018, 83, 14262-14268.

DOI: 10.1021/acs.joc.8b02541 (free Supporting Information)


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Abstract

Sodium hypochlorite pentahydrate (NaClO·5H2O) enables an inexpensive, safe, and rapid oxidation of iodoarenes to provide synthetically useful (diacetoxyiodo)arenes as precursors of various organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.

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Key Words

Hypervalent Iodine Compounds, Sodium Hypochlorite


ID: J42-Y2018