Citation: Li Zhong-Yuan, Jing Kun, Li Qi-Li, Wang Guan-Wu. Palladium-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoester with 2-Aryloxypyridines[J]. Acta Chimica Sinica, ;2019, 77(8): 729-734. doi: 10.6023/A19050190 shu

Palladium-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoester with 2-Aryloxypyridines

Department of Chemistry and Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei 230026

Corresponding author: Wang Guan-Wu, gwang@ustc.edu.cn
Received Date: 22 May 2019
Available Online: 9 August 2019
Fund Project: Project supported by the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000)the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000

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Transition metal-catalyzed C—H activation has attracted extensive attention because of its excellent functional group tolerance and high efficiency. Among them, palladium-catalyzed reactions exhibit versatile catalytic cycles and have mild conditions compared to others. Therefore, the palladium-catalyzed C—H activation has been employed broadly as a practical strategy in synthetic chemistry during the past decade. Since the first example of palladium-catalyzed decarboxylative C—H acylation using α-oxocarboxylic acids was reported in 2008, a lot of substrates have been employed to synthesize acylated products due to the easily available α-oxocarboxylic acids as well as the importance of acylation. However, the transition metal-catalyzed C—H esterification via decarbonylation is still limited. Our group previously developed the first directed C—H esterification of methyl ketoximes and 2-phenylpyridines by using potassium oxalate monoester as the decarboxylative reagent. Encouraged by this impressive result as well as the importance of salicylate derivatives in drug discovery, herein we disclose the efficient palladium-catalyzed decarboxylative esterification of 2-aryloxpyridines. This reaction proceeds smoothly with potassium oxalate monoester, affording the desired products in moderate to good yields (50%~82%). Compared to our previous work, the electron-donating pyridinyloxy (PyO) group as the directing group and six-membered metallocycle intermediate dramatically enhance the practicability and substrate tolerance of the present method. In addition, one of the products has been chosen as the model compound to deprotect the directing group to get the valuable salicylate derivative. The present method not only provides an efficient and convenient protocol for the synthesis of ethyl salicylate derivatives, but also enriches the diversity of Pd(Ⅱ)/Pd(Ⅳ) catalytic reactions. A general procedure for the esterification of 2-aryloxypyridines 1 with potassium oxalate monoester 2 is as following:a mixture of 1 (0.5 mmol), Pd(OAc)₂ (10 mol%), K₂S₂O₈ (1.0 mmol), Ag₂CO₃ (1.0 mmol), 2 (1.0 mmol), D-CSA (0.125 mmol), and 1, 4-dioxane (2.5 mL) in a 25 mL tube was heated at 80℃ for a suitable time. The reaction mixture was cooled to room temperature, and concentrated in vacuo. Purification of the residue by column chromatography on silica gel with petroleum ether and ethyl acetate as the eluent provided the desired product 3.
- palladium catalysis,
- C—H activation,
- 2-aryloxypyridine,
- decarboxylation,
- esterification
1. [1]
2. [2]
  For selected examples, see: (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300. (b) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510. (c) Gandeepan, P.; Cheng, C.-H. J. Am. Chem. Soc. 2012, 134, 5738.
3. [3]
  For selected examples, see: (a) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
4. [4]
  Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837. doi: 10.1021/ja100783c
5. [5]
  (a) Xiao, B.; Fu, Y.; Xu, J.; Gong, T.-J.; Dai, J.-J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468. (b) Dai, H.-X.; Li, G.; Zhang, X.-G.; Stepan, A. F.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 7567.
6. [6]
  For selected examples, see: (a) Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406. (b) Wang, Y.; Gevorgyan, V. Angew. Chem., Int. Ed. 2015, 54, 2255.
7. [7]
  Kakiuchi, F.; Igi, K.; Matsumoto, M.; Hayamizu, T.; Chatani, N.; Murai, S. Chem. Lett. 2002, 3, 396.
8. [8]
  Jia, X.; Zhang, S.; Wang, W.; Luo, F.; Cheng, J. Org. Lett. 2009, 11, 3120. doi: 10.1021/ol900934g
9. [9]
  (a) Ma, W.; Ackermann, L. Chem. Eur. J. 2013, 19, 13925. (b) Liu, B.; Jiang, H.-Z.; Shi, B.-F. J. Org. Chem. 2014, 79, 1521.
10. [10]
  (a) Ackermann, L.; Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154. (b) Chu, J.-H.; Lin, P.-S.; Wu, M.-J. Organometallics 2010, 29, 4058.
11. [11]
  Xu, Y.; Liu, P.; Li, S.-L.; Sun, P. J. Org. Chem. 2015, 80, 1269. doi: 10.1021/jo5026095
12. [12]
  Zhang, C.; Sun, P. J. Org. Chem. 2014, 79, 8457. doi: 10.1021/jo5014146
13. [13]
  (a) Liang, Y.-F.; Li, X.; Wang, X.; Yan, Y.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956. (b) Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508.
14. [14]
  Lou, S.-J.; Chen, Q.; Wang, Y.-F.; Xu, D.-Q.; Du, X.-H.; He, J.-Q.; Mao, Y.-J.; Xu, Z.-Y. ACS Catal. 2015, 5, 2846. doi: 10.1021/acscatal.5b00306
15. [15]
  Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2008, 130, 3304. doi: 10.1021/ja710555g
16. [16]
  Kochi, T.; Urano, S.; Seki, H.; Mizushima, E.; Sato, M.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 2792. doi: 10.1021/ja8097492
17. [17]
  Peng, X.; Zhu, Y.; Ramirez, T. A.; Zhao, B.; Shi, Y. Org. Lett. 2011, 13, 5244. doi: 10.1021/ol2021252
18. [18]
  Wang, S.; Yang, Z.; Liu, J.; Xie, K.; Wang, A.; Chen, X.; Tan, Z. Chem. Commun. 2012, 48, 9924. doi: 10.1039/c2cc34473d
19. [19]
  Liu, B.; Jiang, H.-Z.; Shi, B.-F. Org. Biomol. Chem. 2014, 12, 2538. doi: 10.1039/c4ob00084f
20. [20]
  Li, Z.-Y.; Wang, G.-W. Org. Lett. 2015, 17, 4866. doi: 10.1021/acs.orglett.5b02422
21. [21]
  For a review, see: (a) Wang, G.-W. Top. Organometal. Chem. 2016, 55, 119. For selected examples, see: (b) Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380. (c) Li, Z.-Y.; Li, L.; Li, Q.-L.; Jing, K.; Xu, H.; Wang, G.-W. Chem. Eur. J. 2017, 23, 3285. (d) Jing, K.; Li, Z.-Y.; Wang, G.-W. ACS Catal. 2018, 8, 11875. (e) Jing, K.; Wang, X.-N.; Wang, G.-W. J. Org. Chem. 2019, 84, 161.
22. [22]
  Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654. doi: 10.1021/ja907198n
23. [23]
  For selected example, see:Kim, M.; Park, J.; Sharma, S.; Kim, A.; Park, E.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Chem. Commun. 2013, 49, 925. doi: 10.1039/C2CC38433G
24. [24]
  Mashayekh, S.; Rahmanipour, N.; Mahmoodi, B.; Ahmadi, F.; Motaharian, D.; Shahhosseini, S.; Shafaroodi, H.; Banafshe, H. R.; Shafiee, A.; Navidpour, L. Bioorg. Med. Chem. 2014, 22, 1929. doi: 10.1016/j.bmc.2014.01.041
25. [25]
  Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508. doi: 10.1021/jo502145v
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