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Cu I ‐Catalyzed Synthesis of Propargyl Hydroperoxides Using Molecular Oxygen and Hydroxylamines
Author(s) -
Miner Matthew R.,
Woerpel K. A.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600038
Subject(s) - propargyl , chemistry , yield (engineering) , catalysis , molecular oxygen , oxygen , hydrazine (antidepressant) , active oxygen , medicinal chemistry , organic chemistry , chromatography , materials science , metallurgy
A Cu I ‐catalyzed oxidation of enynes using N ‐hydroxybenzotriazole (HOBt) or N ‐hydroxyphthalimide (NHPI) with molecular oxygen has been developed to yield propargyl hydroperoxides. The reaction occurs under O 2 at 0 °C to afford hydroperoxides in 1–4 h. This method provides an alternative to H 2 O 2 or t BuOOH by using molecular oxygen as the source of oxygen atoms. The resulting hydroperoxides can be protected prior to purification and converted into alkoxyamines upon treatment with hydrazine.