Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

Ayumi Watanabe; Kazunori Miyamoto; Tomohide Okada; Tomotake Asawa; Masanobu Uchiyama

doi:10.1021/acs.joc.8b02541

Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

J Org Chem. 2018 Dec 7;83(23):14262-14268. doi: 10.1021/acs.joc.8b02541. Epub 2018 Nov 8.

Authors

Ayumi Watanabe¹, Kazunori Miyamoto¹, Tomohide Okada², Tomotake Asawa², Masanobu Uchiyama^{1

3}

Affiliations

¹ Graduate School of Pharmaceutical Sciences , The University of Tokyo , Tokyo , Bunkyo-ku 113-0033 , Japan.
² R&D Department of Chemicals , Nippon Light Metal Company, Ltd. , Shimizu-ku , Shizuoka 421-3203 , Japan.
³ Cluster for Pioneering Research (CPR), Advanced Elements Chemistry Laboratory , RIKEN , Wako , Saitama 351-0198 , Japan.

PMID: 30392358
DOI: 10.1021/acs.joc.8b02541

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't