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Synlett 2020; 31(18): 1789-1794
DOI: 10.1055/s-0040-1707264
DOI: 10.1055/s-0040-1707264
letter
Epoxidation of Alkenes with Molecular Oxygen as the Oxidant in the Presence of Nano-Al2O3
This work was supported by the National Natural Science Foundation of China (21673081 and 21971073) and the Natural Science Foundation of Guangdong Province (2018B0303110002 and 2019A1515011468).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707264.
- Supporting Information
Publication History
Received: 24 June 2020
Accepted after revision: 03 August 2020
Article published online:
01 September 2020
© 2020. Thieme. All rights reserved
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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.
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