Citation: Tang Jiansheng, Chen Yao. Recent Advances in Palladium-Catalyzed Synthesis of Coumarins[J]. Chemistry, ;2017, 80(11): 1009-1013. shu

Recent Advances in Palladium-Catalyzed Synthesis of Coumarins

Tang Jiansheng ,
Chen Yao

Hunan First Normal University, Changsha 410205

Received Date: 9 February 2017
Accepted Date: 13 July 2017

Coumarins are a common motif in a variety of naturally occurring and synthetic molecules with interesting biological activities, which are verified to have many pharmacological activities such as cytotoxic, antioxidant, antimicrobial, and anti-inflammatory. Recently, lots of new synthetic methods of coumarins, especially synthetic methods based on highly efficient palladium-catalyzed reactions, have been developed. This paper summarizes the progress in the palladium-catalyzed construction of the coumarin framework in the past twenty years. The main synthetic methods include carbonylation, hydroarylation of alkynes, hydroarylation of alkene and cross-coupling reaction. The review may provide some references for the synthesis of novel lead compounds.
- Coumarin,
- Palladium,
- Carbonylation,
- Hydroarylation of alkynes,
- Hydroarylation of alkene,
- Cross-coupling
1. [1]
  A Gomez-Outes, M Luisa Suarez-Gea, G Calvo-Rojas et al. Curr. Drug Discov. Technol., 2012, 9(2): 83~104.
2. [2]
  D A Horton, G T Bourne, M L Smythe. Chem. Rev., 2003, 103(3): 893~930.
3. [3]
  M S T Gonçalves. Chem. Rev., 2008, 109(1): 190~212.
4. [4]
  Z An, M Catellani, G P Chiusoli. J. Org. Chem., 1989, 371(3): C51~C52.
5. [5]
  D V Kadnikov, R C Larock. J. Org. Chem., 2003, 68(24): 9423~9432.
6. [6]
  H Cao, W J Xiao. Can. J. Chem., 2005, 83(6-7): 826~831.
7. [7]
  B Gabriele, R Mancuso, G Salerno et al. J. Org. Chem., 2008, 73(2): 756~759.
8. [8]
  J Ferguson, F Zeng, H Alper. Org. Lett., 2012, 14(21): 5602~5605.
9. [9]
  K Sasano, J Takaya, N J Iwasawa. J. Am. Chem. Soc., 2013, 135(30): 10954~10957.
10. [10]
  B M Trost, F D Toste, K Greenman. J. Am. Chem. Soc., 2003, 125(15): 4518~4526.
11. [11]
  M Kotani, K Yamamoto, J Oyamada et al. Synthesis, 2004, (9): 1466~1470.
12. [12]
  S Cacchi, G Fabrizi, L Moro et al. Synlett, 1997, 12(12): 1367~1370.
13. [13]
  C Jia, D Piao, T Kitamura et al. J. Org. Chem., 2000, 65(22): 7516~7522.
14. [14]
  K Li, Y Zeng, B Neuenswander et al. J. Org. Chem., 2005, 70(16): 6515~6518.
15. [15]
  T Kitamura, K Otsubo. J. Org. Chem., 2012, 77(6): 2978~2982.
16. [16]
  S Aoki, J Oyamada, T Kitamura. Bull. Chem. Soc. Jpn., 2005, 78(3): 468~472.
17. [17]
  X S Zhang, Z W Li, Z J Shi. Org. Chem. Front., 2014, 1(1): 44~49.
18. [18]
  D Kim, M Min, S Hong. Chem. Commun., 2013, 49(38): 4021~4023.
19. [19]
  G Battistuzzi, S Cacchi, I De Salve et al. Adv. Synth. Catal., 2005, 347(2-3): 308~312.
20. [20]
  F Ulgheri, M Marchetti, O Piccolo. J. Org. Chem., 2007, 72(16): 6056~6059.
21. [21]
  J Wefer, M C Truss, U Jonas. World J. Urol., 2001, 19(5): 312~318.
22. [22]
  E S Rovner, A J Wein. Eur. Urol., 2002, 41(1): 6~14.
23. [23]
  D A Barancelli, A G Salles Jr, J G Taylor et al. Org. Lett., 2012, 14(23): 6036~6039.
24. [24]
  Y Yang, J Han, X Wu et al. Tetrahed. Lett., 2015, 56(24): 3809~3812.
25. [25]
  M J R P Queiroz, A S Abreu, R C Calhelha et al. Tetrahedron, 2008, 64(22): 5139~5146.
26. [26]
  X D Fei, Z Y Ge, T Tang et al. J. Org. Chem., 2012, 77(22): 10321~10328.
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