Journal of Organic Chemistry, volume 83, issue 19, pages 12334-12356

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

Publication typeJournal Article
Publication date2018-09-15
scimago Q2
SJR0.724
CiteScore6.2
Impact factor3.3
ISSN00223263, 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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