Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

A practical method for the preparation of (diacetoxyiodo)­arene ArI­(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allow...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-12, Vol.83 (23), p.14262-14268
Main Authors: Watanabe, Ayumi, Miyamoto, Kazunori, Okada, Tomohide, Asawa, Tomotake, Uchiyama, Masanobu
Format: Article
Language:English
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Summary:A practical method for the preparation of (diacetoxyiodo)­arene ArI­(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl­(tosyloxy)­iodobenzene, iodosylbenzene, iodonium ylide, etc.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02541