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Citation: Xiao Duoduo, Zhang Dengqing, Xiang Yunjie, Li Xianying, Jin Wusong. One-step Synthesis of Pyrimidine-Contained Macrocycles[J]. Chemistry, ;2016, 79(3): 238-242. shu

One-step Synthesis of Pyrimidine-Contained Macrocycles

1.
1. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620;
2.
2. School of Environmental Science and Engineering, Donghua University, Shanghai 201620

Corresponding author: Jin Wusong,
Received Date: 8 July 2015
Available Online: 12 October 2015
Fund Project:

Three pyrimidine-contained π-conjugated macrocycles 1 (1_8mer, 1_10mer and 1_12mer) were synthesized by Pd(PPh₃)₄-catalyzed one-step Suzuki cross-coupling reaction between (3,5-di(5-bromopyrimidine-2-yl)-1-tert-butylbenzene) (2) and (3,5-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-1-tert-butylbenzene) (3). The structures of macrocycles 1 were characterized by ¹H NMR and MALDI-TOF MS, and their optical properties were investigated by UV-Vis absorption and fluorescence spectrometry. The results showed that the one-step method could be efficient in preparing conjugated macrocycles with expended ring size, which provide a new synthetic strategy for the preparation of similar conjugated macrocycles.
- One-step,
- Pyrimidine,
- Macrocycle,
- Synthesis
1. [1]
  [1] M Iyoda, J Yamakawa, M J Rahman. Angew. Chem. Int. Ed., 2011, 50(45):10522~10553.
2. [2]
  [2] I Hwang, W S Jeon, H J Kim et al. Angew. Chem. Int. Ed., 2006, 46(1~2):210~213.
3. [3]
  [3] J Song, S Y Jang, S Yamaguchi et al. Angew. Chem. Int. Ed., 2008, 47(32):6004~6007.
4. [4]
  [4] Y Yamaguchi, S Kobayashi, S Miyamura et al. Angew. Chem. Int. Ed., 2004, 43(3):366~369.
5. [5]
  [5] K Iyoda, K Tanaka, H Shimizu et al. J. Am. Chem. Soc., 2014, 136(6):2389~2396.
6. [6]
  [6] V P Petrov. Mol. Cryst. Liq. Cryst., 2006, 457(1):121~149.
7. [7]
  [7] T Kambara, T Kushida, N Saito et al. Chem. Lett., 1992, 21(4):583~586.
8. [8]
  [8] K T Wong, T S Hung, Y Lin et al. Org. Lett., 2002, 4(4):513~516.
9. [9]
  [9] S Achelle, Y Ramondenc, F Marsais et al. Eur. J. Org. Chem., 2008, (18):3129~3140.
10. [10]
  [10] Z Liu, T Chen, B Liu et al. J. Mater. Chem., 2007, 17:4685~4689.
11. [11]
  [11] O Mongin, A Schuwey, M Vallot et al. Tetrahed. Lett., 1999, 40(48):8347~8350.
12. [12]
  [12] D W J McCallien, J K M Sanders. J. Am. Chem. Soc., 1995, 117(24):6611~6612.
13. [13]
  [13] W Hu, M Ma, X Zhao et al. Tetrahedron, 2012, 68(30):6071~6078.
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