Chinese Journal of Organic Chemistry >
Visible-Light-Induced Benzylic C—H Oxygenation Reaction Using Tetrabutylammonium Tribromide as the Catalyst
Received date: 2021-06-23
Revised date: 2021-08-02
Online published: 2021-08-19
Supported by
National Natural Science Foundation of China(21963010)
The direct oxidative functionalization of the benzylic C—H bonds of alkyl arenes paves a way for the quick synthesis of carbonyl compounds, which is of great significance in organic synthesis. In the past decades, the photooxidative pathways to achieve this reaction have developed rapidly, using relatively green and readily available oxygen as the terminal oxidant under light irradiation. In this paper, a commercially available and inexpensive chemical reagent, tetrabutylammonium tribromide (TBATB), was used to catalyze the photooxidation of the benzylic C—H bonds. Under visible light irradiation and air atmosphere, a catalytic amount of TBATB was utilized to achieve the efficient conversion of alkyl arenes to the corresponding aryl ketones. The reaction is feasible under mild conditions and without any additives, leading to a broad scope of ketone substrates. This method can be an effective supplement to the current benzylic photooxidation reaction systems.
Pengcheng Dai , Liang Xu . Visible-Light-Induced Benzylic C—H Oxygenation Reaction Using Tetrabutylammonium Tribromide as the Catalyst[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4690 -4695 . DOI: 10.6023/cjoc202106041
| [1] | Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B., Chem. Rev. 2006, 106, 2943. |
| [2] | Chen, K.; Zhang, P.; Wang, Y.; Li, H., Green Chem. 2014, 16, 2344. |
| [3] | Guo, Z.; Liu, B.; Zhang, Q.; Deng, W.; Wang, Y.; Yang, Y. Chem. Soc. Rev. 2014, 43, 3480. |
| [4] | Grant, J. T.; Venegas, J. M.; McDermott, W. P.; Hermans, I. Chem. Rev. 2018, 118, 2769. |
| [5] | Marzo, L.; Pagire, S. K.; Reiser, O.; König, B. Angew. Chem. Int. Ed. 2018, 57, 10034. |
| [6] | Gan, Z.; Li, G.; Yang, X.; Yan, Q.; Xu, G.; Li, G.; Jiang, Y.-Y.; Yang, D. Sci. Chin. Chem. 2020, 63, 1652. |
| [7] | Kong, Y.; Xu, W.; Ye, F.; Weng, J. Chin. J. Org. Chem. 2019, 39, 3065. (in Chinese) |
| [7] | ( 孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.) |
| [8] | Zhao, Y.; Zeng, J.; Xia, W. Chin. J. Org. Chem. 2020, 40, 133 (in Chinese) |
| [8] | ( 赵亚婷, 曾俊杰, 夏吾炯, 有机化学, 2020, 40, 133.) |
| [9] | Zhang, Y.; Schilling, W.; Das, S. ChemSusChem 2019, 12, 2898. |
| [10] | Bian, C.; Singh, A. K.; Niu, L.; Yi, H.; Lei, A. Asian J. Org. Chem. 2017, 6, 386. |
| [11] | Zhang, X.; Rakesh, K. P.; Ravindar, L.; Qin, H. L. Green Chem. 2018, 20, 4790. |
| [12] | Hao, L.; Ding, G.; Deming, D. A.; Zhang, Q. Eur. J. Org. Chem. 2019, 2019, 7307. |
| [13] | Fukuzumi, S.; Lee, Y.-M.; Nam, W. ChemSusChem 2019, 12, 3931. |
| [14] | Uygur, M.; Kuhlmann, J. H.; Pérez-Aguilar, M. C.; Piekarski, D. G.; García Mancheño, O. Green Chem. 2021, 23, 3392. |
| [15] | Yi, H.; Bian, C.; Hu, X.; Niu, L.; Lei, A. Chem. Commun. 2015, 51, 14046. |
| [16] | Ohkubo, K.; Mizushima, K.; Iwata, R.; Souma, K.; Suzuki, N.; Fukuzumi, S. Chem. Commun. 2010, 46, 601. |
| [17] | Ohkubo, K.; Fukuzumi, S. Org. Lett. 2000, 2, 3647. |
| [18] | Lechner, R.; Kummel, S.; Konig, B. Photochem. Photobiol. Sci. 2010, 9, 1367. |
| [19] | Zelenka, J.; Svobodova, E.; Tarabek, J.; Hoskovcova, I.; Boguschova, V.; Bailly, S.; Sikorski, M.; Roithova, J.; Cibulka, R. Org. Lett. 2019, 21, 114. |
| [20] | Lesieur, M.; Genicot, C.; Pasau, P. Org. Lett. 2018, 20, 1987. |
| [21] | Li, J.; Bao, W.; Tang, Z.; Guo, B.; Zhang, S.; Liu, H.; Huang, S.; Zhang, Y.; Rao, Y. Green Chem. 2019, 21, 6073. |
| [22] | Tolba, A. H.; Vávra, F.; Chudoba, J.; Cibulka, R. Eur. J. Org. Chem. 2020, 2020, 1579. |
| [23] | Mühldorf, B.; Wolf, R. Chem. Commun. 2015, 51, 8425. |
| [24] | Pokluda, A.; Anwar, Z.; Boguschová, V.; Anusiewicz, I.; Skurski, P.; Sikorski, M.; Cibulka, R. Adv. Synth. Catal. 2021, DOI: 10.1002/adsc.202100024. |
| [25] | Pandey, G.; Pal, S.; Laha, R. Angew. Chem. Int. Ed. 2013, 52, 5146. |
| [26] | Li, S.; Zhu, B.; Lee, R.; Qiao, B.; Jiang, Z. Org. Chem. Front. 2018, 5, 380. |
| [27] | Zhu, X.; Liu, Y.; Liu, C.; Yang, H.; Fu, H. Green Chem. 2020, 22, 4357. |
| [28] | Santra, S. K.; Szpilman, A. M. J. Org. Chem. 2021, 86, 1164. |
| [29] | Zu, W.; Day, C.; Wei, L.; Jia, X.; Xu, L. Chem. Commun. 2020, 56, 8273. |
| [30] | Wei, L.; Zhang, J.; Xu, L. ACS Sustainable Chem. Eng. 2020, 8, 13894. |
| [31] | Wei, L.; Wei, Y.; Zhang, J.; Xu, L. Green Chem. 2021, 23, 4446. |
| [32] | Gazi, S.; Ananthakrishnan, R. RSC Adv. 2012, 2, 7781. |
| [33] | Nikitas, N. F.; Tzaras, D. I.; Triandafillidi, I.; Kokotos, C. G. Green Chem. 2020, 22, 471. |
| [34] | Fujita, K.-i.; Tamura, R.; Tanaka, Y.; Yoshida, M.; Onoda, M.; Yamaguchi, R. ACS Catal. 2017, 7, 7226. |
| [35] | Jayaprakash, H.; Guo, L.; Wang, S.; Bruneau, C.; Fischmeister, C. Eur. J. Org. Chem. 2020, 2020, 4326. |
| [36] | Ye, D.; Liu, Z.; Sessler, J. L.; Lei, C. Chem. Commun. 2020, 56, 11811. |
| [37] | Liu, K.-J.; Duan, Z.-H.; Zeng, X.-L.; Sun, M.; Tang, Z.; Jiang, S.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 10293. |
| [38] | Dutta, U.; Lupton, D. W.; Maiti, D. Org. Lett. 2016, 18, 860. |
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