Issue 10, 2021

Aerobic α-hydroxylation of 2-Me-1-tetralone in 1-alkyl-3-methylimidazolium ionic liquids

Abstract

The aerobic α-hydroxylation of 2-Me-1-tetralone was investigated in imidazol-based ionic liquids (ILs), where reactions in 1-alkyl-3-methylimidazolium tetrafluoroborates were found to generate considerable products. By correlating the conversion at 2 h with viscosity, relative permittivity and the ET(30) value of ILs, we found that the local polarity in ILs represented by the ET(30) value or the chemical shift of α-proton at the substrate was the critical factor influencing the reaction rate. Furthermore, two-dimensional nuclear Overhauser effect spectroscopy (2D NOESY) was used to characterize the distribution of 2-Me-1-tetralone in ILs. As a result, the mesoscopic structures in ILs were recommended to have crucial influences on the distribution of the substrate in ILs, and the caused local polarity could affect the activation of 2-Me-1-tetralone. These findings revealed the solvent effects of ILs with different structures on the α-hydroxylation of 2-Me-1-tetralone, and may encourage the explorations of more types of aerobic oxidations in ILs.

Graphical abstract: Aerobic α-hydroxylation of 2-Me-1-tetralone in 1-alkyl-3-methylimidazolium ionic liquids

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2020
Accepted
19 Feb 2021
First published
20 Feb 2021

Phys. Chem. Chem. Phys., 2021,23, 5864-5869

Aerobic α-hydroxylation of 2-Me-1-tetralone in 1-alkyl-3-methylimidazolium ionic liquids

Y. Wang, Z. Wen, Y. Zhang, X. Wang, J. Yao and H. Li, Phys. Chem. Chem. Phys., 2021, 23, 5864 DOI: 10.1039/D0CP06047J

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