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  4. Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
 
research article

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

Alazet, Sebastien
•
Preindl, Johannes
•
Simonet-Davin, Raphael
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September 15, 2018
The Journal of Organic Chemistry

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 hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.

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Type
research article
DOI
10.1021/acs.joc.8b02068
Web of Science ID

WOS:000447118100085

Author(s)
Alazet, Sebastien
Preindl, Johannes
Simonet-Davin, Raphael
Nicolai, Stefano
Nanchen, Annik
Meyer, Thierry
Waser, Jerome
Simonet Davin, Raphael
Preindl, Johannes
Date Issued

2018-09-15

Published in
The Journal of Organic Chemistry
Volume

83

Issue

19

Start page

12334

End page

12356

URL

ChemRxiv preprint

https://dx.doi.org/10.26434/chemrxiv.6946058
Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSO  
GSCP  
FunderGrant Number

EU funding

334840

FNS

CRSII5_171026

Available on Infoscience
December 28, 2018
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/153223
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