Epoxidation of Alkenes with Molecular Oxygen as the Oxidant in the Presence of Nano-Al₂O₃

Abstract

The nano-Al₂O₃-promoted epoxidation of alkenes with molecular oxygen as the oxidant has been developed, providing an efficient route to a variety of epoxides in moderate to excellent yields. The environmentally friendly and efficient nano-Al₂O₃ catalyst could be easily recovered and reused five times without significant loss of activity.

Key words

alkenes - nano-alumina - epoxidation - epoxides - molecular oxygen

Publication History

Received: 24 June 2020

Accepted after revision: 03 August 2020

Article published online:
01 September 2020

• References and Notes

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• 17 Typical Procedure for the Synthesis of Epoxide 2a To a 25 mL dried Schlenk tube was added the mixture of nano-Al₂O₃ (10.2 mg), alkene 1a (1.0 mmol), 3,5,5-trimethylhexanal (3.0 mmol) in dry MeCN (5 mL) successively. The resulting mixture was stirred at 60 °C for 24 h under 1 atm of O₂. After the reaction was completed, the reaction mixture was cooled to room temperature, diluted with EtOAc (25 mL), and filtered. After removing the solvent under vacuum, the crude product was separated by column chromatography on silica gel using PE–EtOAc as eluent to give the product 2a as a pale-yellow oil; yield 84%. IR (KBr): 3060, 2933, 1450, 966, 859, 749, 543 cm^–1. MS (EI): m/z = 174 [M⁺]. ¹H NMR (500 MHz, CDCl₃): δ = 7.27–7.11 (m, 5 H), 2.95 (d, J = 3.5 Hz, 1 H), 2.19–2.13 (m, 1 H), 2.02–1.97 (m, 1 H), 1.92–1.81 (m, 2 H), 1.53–1.41 (m, 2 H), 1.38–1.31 (m, 1 H), 1.24–1.15 (m, 1 H). ¹³C NMR (126 MHz, CDCl₃): δ = 142.6, 128.3, 127.2, 125.3, 61.9, 60.2, 28.9, 24.8, 20.2, 19.8.
• 18 CCDC 2019579 contains the supplementary crystallographic data for compound 2r. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
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