Chemoselective benzylic oxidation of alkyl-substituted aromatics with singlet molecular oxygen generated from trans-3, 5 hydroperoxy-3, 5 dimethyl-1, 2-dioxolan-3-yl ethaneperoxate. Issue 24 (17th December 2022)

• Record Type: Journal Article
• Authors: Najminejad, Zohreh
• Is Part Of: Synthetic communications. Volume 52:Issue 24(2022)
• Page Start: 2301
• Page End: 2310
• Publication Date: 2022-12-17
• Subjects: Alkyl-substituted aromatics -- oxidation -- singlet molecular oxygen -- trans-3, 5-hydroperoxy-3, 5-dimethyl-1, 2-dioxolan-3-yl ethaneperoxate; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2022.2145226
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Chemoselective benzylic oxidation of alkyl-substituted aromatics to carbonyl compounds was efficiently achieved with singlet molecular oxygen generated from trans- 5-hydroperoxy-3, 5-dimethyl-1, 2-dioxolane-3-yl ethaneperoxate. The singlet molecular oxygen was generated in situ from fragmentation trans -5-hydroperoxy-3, 5-dimethyl-1, 2-dioxolane-3-yl ethaneperoxate in the presence of KOH. All the reactions proceeded smoothly at room temperature to afford the products in good-to-excellent yields within short reaction times. Also, the method is compatible with functional groups including, amines, sulfides, and allylic CH2 . Graphical Abstract: UF0001