Organocatalytic Oxidative Dehydrogenation of Dihydroarenes by Dioxygen Using 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2
Abstract
:Introduction
Results and Discussion
Comparison of different benzoquinones and anthraquinones combined with NaNO2
Optimization of the catalyst loading amounts, reaction time, and temperature for DDQ/NaNO2
Entry | Catalyst loading (mol%) | Conversion (%) | Products and selectivity (%) | ||
---|---|---|---|---|---|
DDQ | NaNO2 | ATC | AQ | ||
1 | 1 | 1 | 19 | >99 | - |
2 | 2 | 2 | 35 | >99 | - |
3 | 3 | 3 | 56 | >99 | - |
4 | 5 | 5 | >99 | 99 | 1 |
5 | 10 | 10 | >99 | 99 | 1 |
6 b | 5 | 5 | 64 | >99 | - |
7 b | 10 | 10 | >99 | >99 | - |
Entry | Catalyst loading (mol%) | Time (h) | Conv. (%) | Products and selectivity(%) | ||
---|---|---|---|---|---|---|
DDQ | NaNO2 | ATC | AQ | |||
1 | 5 | 5 | 1 | 42 | >99 | - |
2 | 5 | 5 | 3 | 47 | >99 | - |
3 | 5 | 5 | 5 | 54 | >99 | - |
4 | 5 | 5 | 8 | >99 | 99 | 1 |
5 | 5 | 0 | 5 | 10 | >99 | - |
6 | 0 | 5 | 5 | 8 | >99 | - |
7 | 0 | 0 | 5 | 3 | >99 | - |
8 b | 0 | 0 | 5 | n.d. | - | - |
Oxidative dehydrogenation of variety of dihydroarenes with DDQ/NaNO2
Entry | Substrates | Conversion (%) | Product and selectivity/yield (%) |
---|---|---|---|
1 | | >99 | |
2 | | >99 | |
3 | | 91 | |
4 | | 77 | |
5 | | 68 | |
6b | | 32 | |
The proposed catalytic cycle
Conclusions
Experimental
General
Oxidation reaction and products analysis
Acknowledgements
References and Notes
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Zhang, W.; Ma, H.; Zhou, L.; Sun, Z.; Du, Z.; Miao, H.; Xu, J. Organocatalytic Oxidative Dehydrogenation of Dihydroarenes by Dioxygen Using 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2. Molecules 2008, 13, 3236-3245. https://doi.org/10.3390/molecules13123236
Zhang W, Ma H, Zhou L, Sun Z, Du Z, Miao H, Xu J. Organocatalytic Oxidative Dehydrogenation of Dihydroarenes by Dioxygen Using 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2. Molecules. 2008; 13(12):3236-3245. https://doi.org/10.3390/molecules13123236
Chicago/Turabian StyleZhang, Wei, Hong Ma, Lipeng Zhou, Zhiqiang Sun, Zhongtian Du, Hong Miao, and Jie Xu. 2008. "Organocatalytic Oxidative Dehydrogenation of Dihydroarenes by Dioxygen Using 2,3-Dichloro-5,6-dicyano-benzoquinone (DDQ) and NaNO2" Molecules 13, no. 12: 3236-3245. https://doi.org/10.3390/molecules13123236