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2013 , Vol. 33 >Issue 9: 2022 - 2027

DOI: https://doi.org/10.6023/cjoc201303022

研究简报

微波辅助合成芳烃钌(II)配合物[(η6-RC6H5)Ru(m-MOPIP)Cl]Cl

  • 吴琼 ,
  • 吴剑 ,
  • 梅文杰 ,
  • 姚骏骅 ,
  • 吴韦黎 ,
  • 陈燕华 ,
  • 陶韵伊
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  • a 广东药学院药科学院 广州 510006;
    b 中山大学测试中心 广州 510275

收稿日期: 2013-03-15

  修回日期: 2013-04-06

  网络出版日期: 2013-05-06

基金资助

广东省科技计划(No. 2013J4100072);广州市科技计划(No. 7411791521750)资助项目

收起

Microwave-Assisted Synthesis of Arene Ru(II) Complexes[(η6-RC6H5)Ru(m-MOPIP)Cl]Cl

  • Wu Qiong ,
  • Wu Jian ,
  • Mei Wenjie ,
  • Yao Junhua ,
  • Wu Weili ,
  • Chen Yanhua ,
  • Tao Yunyi
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  • a School of Pharmacy, Guangdong Pharmaceutical University, Gongzhou 510006;
    b Instrumental Analysis and Research Center, Sun Yat-sen University, Gongzhou 510275

Received date: 2013-03-15

  Revised date: 2013-04-06

  Online published: 2013-05-06

Supported by

Project supported by the Science and Technology Planning Project of Guangdong Province (No. 2013J4100072) and the Science and Technology Planning Project of Guangzhou City (No. 7411791521750)

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摘要

运用微波辅助合成技术, 在二氯甲烷溶液中, 60℃条件下, Pyrex管中微波辐射30 min制备得到芳烃钌(II)化合物[(η6-RC6H5)Ru(m-MOPIP)Cl]Cl (R=H 3a, R=CH3 3b; m-MOPIP=2-(3-甲氧苯基)-咪唑并[4,5f][1,10]菲啰啉), 反应产率分别为90%和91%, 目标化合物运用1H NMR, 13C NMR, IR, ESI-MS以及1H-1H COSY进行表征; 在相同条件下SiC管中, 屏蔽微波辐射对反应的影响, 3a和3b的产率分别为89%和90%, 说明微波“非热效应”对芳烃钌(II)配合物的合成没有显著影响.

关键词： 微波辅助合成; 2-(3-甲氧基苯基)-咪唑并[4,5f][1,10]菲啰啉; 芳烃钌(II)配合物

本文引用格式

吴琼 , 吴剑 , 梅文杰 , 姚骏骅 , 吴韦黎 , 陈燕华 , 陶韵伊 . 微波辅助合成芳烃钌(II)配合物[(η6-RC6H5)Ru(m-MOPIP)Cl]Cl[J]. 有机化学, 2013 , 33(9) : 2022 -2027 . DOI: 10.6023/cjoc201303022

Abstract

Two arene Ru(II) complexes[(η6-RC6H5)Ru(m-MOPIP)Cl]+ (R=H 3a, R=CH3 3b; m-MOPIP=2-(3-meth- oxyphenyl)imidazole[4,5-f][1,10]phenanthroline) were prepared under the microwave irradiation at 60 ℃ for 30 min in Pyrex vessel with the yield of about 90% and 91%, and the target compounds were characterized by 1H NMR, 13C NMR, IR, ESI-MS and 1H-1H COSY spectra. At the same reaction conditions, application of SiC vessel to screen the effect of microwave irradiation, 3a and 3b were obtained with the yield of about 89% and 90%. These results indicated that the microwave "non-thermal effect" has no obvious influence on the synthesis of arene Ru(II) complexes.

Key words： microwave-assisted synthesis; 2-(3-methoxyphenyl)imidazole[4,5f][1,10]phenanthroline; arene Ru(II) complexes

参考文献

[1] (a) Leadbeater, N. E.; Shoemaker, K. M. Organometallics 2008, 27, 1254.
(b) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
(c) Zhang, Z.; Wang, Q.; Wu, Q.; Hu, X.-Y.; Wang, C.-X.; Mei, W.-J.; Tao, Y.-Y.; Wu. W.-L.; Zheng, W.-J. Chem. J. Chin. Univ. 2012, 33, 2441(in Chinese).
(张召, 王淇, 吴琼, 胡晓莹, 王成蹊, 梅文杰, 陶韵伊, 吴韦黎, 郑文杰, 高等学校化学学报, 2012, 33, 2441.)
(d) Mallikarjuna, N. N.; Thomas, F. S.; Rajender, S. V. Acc. Chem. Res. 2011, 44, 469.
(e) Albrecht, C.; Gauthier, S.; Wolf, J.; Scopelliti, R.; Severin, K. Eur. J. Inorg. Chem. 2009, 1003.
[2] Liu, Y.; Hammitt, R.; Lutterman, D. A.; Thummel, R. P.; Turro, C. Inorg. Chem. 2007, 46, 6011.
[3] Abrahamsson, M.; Becker, H. C.; Hammarstroem, L.; Bonnefous, C.; Chamchoumis, C.; Thummel, R. P. Inorg. Chem. 2007, 46, 10354.
[4] (a) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
(b) Therrien, B.; Süss-Fink, G.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J. Angew. Chem. Int. Ed. 2008, 47, 3773.
(c) Severin, K.; Bergs, R.; Beck, W. Angew. Chem., Int. Ed. 1998, 37, 1634.
(d) Smith, G. S.; Therrien, B. Dalton Trans. 2010, 40, 10793.
[5] (a) Nowak-Sliwinska, P.; Beijnum, J. R.; Casini, A.; Nazarov, A. A.; Wagniėres, G.; Bergh, H.; Dyson, P. J.; Griffioen, A. W. J. Med. Chem. 2011, 54, 3895.
(b) Chatterjee, S.; Kundu, S.; Bhattacharyya, A.; Hartinger, C. G.; Dyson, P. J. J. Biol. Inorg. Chem. 2008, 13, 1149.
(c) Yin, J.; Guan, J.-T.; Yu, G.-A.; Liu, S.-H. Chin. J. Org. Chem. 2004, 24, 117 (in Chinese).
(尹军, 关金涛, 余广鳌, 刘盛华, 有机化学, 2004, 24, 117.)
[6] Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietto, M.; Laurenczy, G.; Geldbach, T. J.; Sava, G.; Dyson, P. J. J. Med. Chem. 2005, 48, 4161.
[7] Martínez, A.; Suárez, J.; Shand, T.; Magliozzo, R. S.; Sánchez-Delgado, R. A. J. Inorg. Biochem. 2011, 105, 39.
[8] (a) Tan, L.-F.; Liu, X.-H.; Chao, H.; Ji, L.-N. J. Inorg. Biochem. 2007, 101, 56.
(b) Chen, T.-F.; Mei, W.-J.; Wong, Y.-S.; Liu, J.; Liu, Y.; Xie, H.-S.; Zheng, W.-J. Med. Chem. Commun. 2010, 1, 73.
[9] (a) Mei, W.-J.; Liu, J.; Zheng, K.-C.; Lin, L. J.; Chao, H.; Li, A.-X.; Yun, F.-C.; Ji, L.-N. Dalton Trans. 2003, 1352.
(b) Sun, D.-D.; Wang, W.-Z.; Mao, J.-W.; Mei, W.-J.; Liu, J. Bioorg. Med. Chem. Let. 2012, 22, 102.
[10] Therrien, B. Coord. Chem. Rev. 2009, 253, 493.
[11] (a) Canivet, J.; Karmazin-Brelot, L.; Süss-Fink, G. J. Organomet. Chem. 2005, 690, 3202.
(b) Renfrew, A. K.; Egger, A. E.; Scopelliti, R.; Hartinger, C. G.; Dyson, P. J. C. R. Chim. 2010, 13, 1144.
(c) Süss-Fink, G.; Khan, F. A.; Jeanneret, L. J.; Dyson, P. J.; Renfrew, A. K. J. Cluster. Sci. 2010, 21, 313.
[12] (a) Zelonka, R. A.; Baird, M. C. Can. J. Chem. 1972, 50, 3063.
(b) Bennett, M. A.; Huang, T. N.; Matheson, T. W.; Smith, A. K. Inorg. Synth. 1982, 21, 74.
[13] Winkhaus, G.; Singer, H. J. Organomet. Chem. 1967, 7, 487.
[14] Liu, H. K.; Sadler, P. J. Acc. Chem. Res. 2011, 44, 349.
[15] (a) Fang, X.; Hutcheon, R.; Scola, D. A. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2526.
(b) Hawangchu, Y.; Atong, D.; Sricharoenchaikul, V. Int. J. Chem. React. Eng. 2010, 8, 65.
[16] Wang, Q.; Wang, C.-X.; Sun, F.-Q.; He, L.-M.; Wu, Q.; Liang, B.-H.; Qiu, Y.-B.; Mei, W.-J. Acad. J. Guangdong College Pharm. 2012, 28, 17 (in Chinese).
(王淇, 王成蹊, 孙福强, 贺丽敏, 吴琼, 梁炳焕, 邱永彬, 梅文杰, 广东药学院学报, 2012, 28, 17.)
[17] Marky, L. A.; Breslauer, K. J. Biopolymers 1987, 26, 1601.
[18] Li, Y.-J.; Huang, H.-M.;Gao, J.-R.; Jia, J.-H.; Dong, H.-Q.; Han, L.; Sheng, W.-J. Chin. J. Org. Chem. 2011, 31, 1286 (in Chinese).
(李郁锦, 黄焕明, 高建荣, 贾建洪, 董华清, 韩亮, 盛卫坚, 有机化学, 2011, 31, 1286.)
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