Citation: Shao Tianju, Jiang Zhiyong. Visible Light Mediated Photocatalytic Aerobic Dehydrogenation: A General and Direct Approach to Access 2, 3-Dihydro-4-Pyridones and 4-Quinolones[J]. Acta Chimica Sinica, ;2017, 75(1): 70-73. doi: 10.6023/A16080407 shu

Visible Light Mediated Photocatalytic Aerobic Dehydrogenation: A General and Direct Approach to Access 2, 3-Dihydro-4-Pyridones and 4-Quinolones

Shao Tianju ,
Jiang Zhiyong ^*,,

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng 475004

Corresponding author: Jiang Zhiyong, chmjzy@henu.edu.cn
Received Date: 13 August 2016

Fund Project: and the Science and Technology Department of Henan Province 14IRTSTHN006and the Science and Technology Department of Henan Province 152300410057National Natural Science Foundation of China 21672052National Natural Science Foundation of China 21072044

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A visible-light-induced photocatalytic aerobic dehydrogenation of 4-piperidones and 2, 3-dihydro-4-quinolones has been developed. By utilizing dicyanopyrazine-derived chromophore (DPZ) as the photocatalyst, the dehydrogenation could provide 2, 3-dihydro-4-pyridones and 4-quinolones with satisfactory results (up to 75% yield). The current methodology presents a direct, sustainable and highly atom-economic approach to access these valuable N-containing heterocycles.
- visible light photocatalysis,
- DPZ,
- dehydrogenation,
- pyridone,
- quinolone
1. [1]
  For selected examples, see: (a) Kozikowski, A. P.; Park, P.-U. J. Org. Chem. 1990, 55, 4668; (b) Shintani, R.; Hayashi, T. Nat. Protoc. 2007, 2, 2903; (c) Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2005, 7, 2433; (d) Ye, X. M.; Konradi, A. W.; Smith, J.; Xu, Y.-Z.; Dressen, D.; Garofalo, A. W.; Marugg, J.; Sham, H. L.; Truong, A. P.; Jagodzinski, J.; Pleiss, M.; Zhang, H.; Goldbach, E.; Sauer, J.-M.; Brigham, E.; Bova, M.; Basi, G. S. 2010, 20, 2195; (e) Gordeev, M. F.; Yuan, Z. Y. J. Med. Chem. 2014, 57, 4487.
2. [2]
  For selected examples, see: (a) Huang, X.; Liu, Z.J. Org. Chem. 2002, 67, 6731; (b) Shintani, R.; Yamagami, T.; Kimura, T.; Hayashi, T. Org. Lett. 2005, 7, 5317; (c) Biswas, K.; Peterkin, T. A. N.; Bryan, M. C.; Arik, L.; Arik, L.; Lehto, S. G.; Sun, H.; Hsieh, F.-Y.; Xu, C.; Fremeau, R. T.; Allen, J. R. J. Med. Chem. 2011, 54, 7232; (d) Brouwer, C.; Jenko, K.; Zoghbi, S. S.; Innis, R. B.; Pike, V. W. J. Med. Chem. 2014, 57, 6240; (e) Bichovski, P.; Haas, T. M.; Kratzert, D.; Streuff, J. Chem. Eur. J. 2015, 21, 2339; (f) Liu, J.; Li, Z.; Tong, P.; Xie, Z.; Zhang, Y.; Li, Y. J. Org. Chem. 2015, 80, 1632.
3. [3]
  (a) Cecchetti, V.; Parolin, C.; Moro, S.; Pecere, T.; Filipponi, E.; Calistri, A.; Tabarrini, O.; Gatto, B.; Palumbo, M.; Fravolini, A.; Palu, G. J. Am. Chem. Soc. 2000, 43, 3799; (b) Wang, S.; Lin, J.; He, P.; Zuo, J.; Long, Y. Acta Chim. Sinica 2014, 72, 906 (王沈丰, 林建平, 何佩岚, 左建平, 龙亚秋, 化学学报, 2014, 72, 906.); (c) Enoki, Y.; Ishima, Y.; Tanaka, R.; Sato, K.; Kimachi, K.; Shirai, T.; Watanabe, H.; Chuang, V. T. G.; Fujiwara, Y.; Takeya, M.; Otagiri, M.; Maruyama, T. Plos One 2015, DOI:10.1371/journal.pone.0130248.
4. [4]
  (a) Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 993; (b) Šebesta, R.; Pizzuti, M. G.; Boersma, A. J.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2005, 1711; (c) Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566; (d) Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701; (e) Niphaki, M. J.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2010, 75, 6793.
5. [5]
  For a selected review, see:Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, M. M. Curr. Org. Chem. 2005, 9, 141.
6. [6]
  For selected examples, see: (a) Werner, W. Tetrahedron 1969, 25, 255; (b) Chen, B.; Huang, X.; Wang, J. Synthesis 1987, 482; (c) Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; Derisi, J. L.; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.
7. [7]
  Camps, R. Chem. Ber. 1899, 32, 3228. doi: 10.1002/(ISSN)1099-0682
8. [8]
  For selected examples, see: (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421; (b) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
9. [9]
  For selected examples, see: (a) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101; (b) Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001.
10. [10]
  (a) Tois, J.; Vahermo, M.; Koskinen, A. Tetrahedron Lett. 2005, 46, 735; (b) Huang, J.; Chen, Y.; King, A. O.; Dilmeghani, M.; Larsen, R. D.; Faul, M. M. Org. Lett. 2008, 10, 2609; (c) Ward, T. R.; Turunen, B. J.; Haack, T.; Neuenswander, B.; Shadrick, W.; Georg, G. I. Tetrahedron Lett. 2009, 50, 6494; (d) Mphahlele, M. J. J. Heterocycl. Chem. 2010, 47, 1; (e) Lange, J.; Bissember, A. C.; Banwell, M. G.; Cade, I. A.Aust. J. Chem. 2011, 64, 454.
11. [11]
  For selected recent reviews, see: (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322; (b) Zhao, J.; Wu, W.; Sun, J.; Guo, S. Chem. Soc. Rev. 2013, 42, 5323; (c) Lang, X.; Chen, X.; Zhao, J. Chem. Soc. Rev. 2014, 43, 473; (d) Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355; (e) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985; (f) Xuan, J.; Zhang, Z.-G.; Xiao, W.-J.Angew. Chem., Int. Ed. 2015, 54, 15632; (g) Beatty, J. W.; Stephenson, C. R. J. Acc. Chem. Res. 2015, 48, 1474; (h) Wei, G.; Basheer, C.; Tan, C.-H.; Jiang, Z. Tetrahedron Lett. 2016, 57, 3801.
12. [12]
  (a) Zhao, Y.; Zhang, C.; Chin, K. F.; Pytela, O.; Wei, G.; Liu, H.; Bureš, F.; Jiang, Z. RSC Adv. 2014, 4, 30062; (b) Liu, X.; Ye, X.; Bureš, F.; Liu, H.; Jiang, Z. Angew. Chem., Int. Ed. 2015, 54, 11443. (c) Wei, G.; Zhang, C.; Bureš, F.; Ye, X.; Tan, C.-H.; Jiang, Z. ACS Catal. 2016, 6, 3708; (d) Zhang, C.; Li, S.; Bureš, F.; Lee, R.; Ye, X.; Jiang, Z. ACS Catal. 2016, 6, 6853.
13. [13]
  See the supporting information for details.
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