CuI‐Catalyzed Synthesis of Propargyl Hydroperoxides Using Molec­ular Oxygen and Hydroxylamines. Issue 10 (21st March 2016)

• Record Type: Journal Article
• Authors: Miner, Matthew R.; Woerpel, K. A.
• Is Part Of: European journal of organic chemistry. Issue 10(2016)
• Page Start: 1860
• Page End: 1866
• Publication Date: 2016-03-21
• Subjects: Peroxides -- Oxidation -- Enynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600038
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 O2 at 0 °C to afford hydroperoxides in 1–4 h. This method provides an alternative to H2 O2 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. Abstract : Propargyl peroxides are synthesized by a Cu I ‐catalyzed peroxidation of enynes using molecular oxygen and N ‐hydroxybenzotriaxole (HOBt) or N ‐hydroxyphthalimide (NHPI). Molecular oxygen is used as the source of oxygen atoms, avoiding the use of H2 O2 or t BuOOH.