3 research outputs found
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
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
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox Catalyzed Ring Expansion
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
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox Catalyzed Ring Expansion
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, <i>t</i>Bu-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