Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox Catalyzed Ring Expansion

09 August 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Azides are building blocks of increasing importance in synthetic chemistry, chemical biology and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its highly hazardous nature. We further introduce and study two derivatives, tBu-ABX and ABZ (azidobenziodazolone). ABZ displayed a similar reactivity but a better safety profile than ABX, and could be used in established photoredox- and metal-mediated azidation processes, as well as in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.


hypervalent iodine
photoredox catalysis
zhdankin reagent
Safety studies
Azidobenziodazolone (ABZ)


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.