Journal of Organic Chemistry, volume 83, issue 19, pages 12334-12356
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion.
Sébastien Alazet
1
,
Johannes Preindl
1
,
Raphael Simonet Davin
1
,
Stefano Nicolai
1
,
Annik Nanchen
2
,
Thierry Meyer
3
,
Jerome Waser
1
2
Process Safety, TÜV SÜD Schweiz AG, CH-4002 Basel, Switzerland
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Publication type: Journal Article
Publication date: 2018-09-15
Journal:
Journal of Organic Chemistry
scimago Q2
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
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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