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Environmentally Friendly Room Temperature Synthesis of 1-tetralone over Layered Double Hydroxide-Hosted Sulphonato-Salen-Nickel(II) Complex

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Green and Sustainable Chemistry 2023年第1期13卷 9-22页

作者： Samiran Bhattacharjee Mohammad A. Matin Hasina Akhter Simol Anowar Hosen Centre for Advanced Research in Sciences (CARS) University of Dhaka Dhaka Bangladesh

1-tetralone, a useful synthetic intermediate in the manufacture of pharmaceuticals, agrochemicals and dyes, can be prepared by liquid phase catalytic oxidation of tetralin. Selective oxidation of tetralin to 1-tetralone is still a big challenge with low-temperature processes using environmentally friendly routes even after decades of research. Herein, we demonstrate room-temperature oxidation of tetralin to 1-tetralone over layered double hydroxide-hosted sulphonato-salen-nickel(II) complex, LDH-[Ni-salen]. The layered double hydroxide-hosted sulphonato-salen-nickel(II) compound was characterized by powder X-ray diffraction, Fourier transform infrared spectrometer (FTIR), UV-Visible diffuse reflectance spectra, scanning electron microscopy (SEM) and elemental analysis. The theoretical calculations of free sulphonato-salen-nickel(II) complex using Density Functional Theory/CAM-B3LYP at the 6-311++ G(d,p) level of theory were also used to determine the orientation of the Ni-salen compound within the layered structure. The immobilized compound, LDH-[Ni-salen] was found to be an effective reusable catalyst for the oxidation of tetralin to 1-tetralone using a combination of trimethylacetaldehyde and molecular oxygen (14.5 psi) and at 25°C. At 45.5% conversion, tetralin was converted to 1-tetralone with 77.2% selectivity at room temperature and atmospheric pressure after 24 h. The catalyst recycles test and hot filtration experiment showed that oxidation proceeded through Ni(II) sites in LDH-[Ni-salen]. The catalysts were reused several times without losing their catalytic activity and selectivity. The present results may provide a convenient strategy for the preparation of 1-tetralone using layered double hydroxide-based heterogeneous catalyst at ambient temperature for industrial application in near future.

关键词： Sulphonato-Salen-Nickel(II) Layered Double Hydroxide Tetralin Oxidation Room Temperature 1-tetralone

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Mannich Reaction with Arylamine as Amino Component(Ⅶ)

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Chemical Research in Chinese Universities 1988年第2期 67-71页

作者： Zhao Dong, Xu Xiujuan, Liu Yao and Chen Guangxu(K.H. Chen) (Department of Chemistry, Beijing Normal University, Beijing)

2-Arylaminomethyl-1-tetralone and 2-arylaminomethyl-6 (or 7)-methyl (or me thoxy) -1 - tetralone were synthesized by the Mannich reaction which was carried out directly on the condensation product of arylamine with formaldehyde or arylamine-HC1 and 1-tetralone derivatives in ethanol-HCl solution. Twenty-five compounds were obtained in high yields.

关键词： Mannich reaction Mannich base 1-tetralone Arylamine.

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