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Recent applications of the Zhdankin reagent in organic synthesis

journal contribution
posted on 2023-05-20, 10:21 authored by Angus OldingAngus Olding, Curtis HoCurtis Ho

Hypervalent iodine reagents have rapidly become vital synthetic tools in organic chemistry as stoichiometric oxidants and electrophilic sources of various functional groups such as F, CN, and alkynes.[13] Many such reagents are now known, with prominent examples such as Dess–Martin periodinane and 2-iodoxybenzoic acid being commercially available. In 1996, the Zhdankin reagent, 1-azido-1,2-benziodoxol-3(1H)-one (3) was first prepared[4] from 1-hydroxy-1,2-benziodoxol-3(1H)-one (1) and trimethylsilyl azide (Scheme 1). This hypervalent iodine compound can also be efficiently prepared from iodosobenzoic acid (2).[5] Compound 3 has been shown to primarily act as a source of radical azide.[5,6] Radical reactivity can be initiated thermally or with a peroxide catalyst. The use of this reagent in synthesis has grown considerably since 2013, which may relate to the rise of photoredox catalysis. The latter methodology allows the generation of radicals under particularly mild conditions. The Zhdankin reagent is frequently employed in tandem with a metal catalyst such as copper[712] or iron.[13,14] This article highlights some notable applications of molecule 3 that have appeared since 2016.

History

Publication title

Australian Journal of Chemistry

Volume

72

Issue

8

Pagination

646-648

ISSN

0004-9425

Department/School

School of Natural Sciences

Publisher

C S I R O Publishing

Place of publication

150 Oxford St, Po Box 1139, Collingwood, Australia, Victoria, 3066

Rights statement

Copyright CSIRO 2019

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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