研究论文

无催化剂微波促进下C—O, C—N 和C—S 交叉偶联反应研究

  • 袁艳琴 ,
  • 郭圣荣 ,
  • 莫建军 ,
  • 钱利 ,
  • 石泽凤
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  • 丽水学院化学化工系 丽水 323000

收稿日期: 2011-08-30

  修回日期: 2011-11-03

  网络出版日期: 2012-04-24

基金资助

浙江省自然科学基金基金(No. Y407240)和丽水学院重点科研(No. KZ20H03)资助项目.

Rapid and Highly Efficient Microwave-Assisted C—N, C—O and C— S Coupling Reactions without a Transition-Metal Catalyst

  • Yuan Yanqin ,
  • Guo Shengrong ,
  • Mo Jianjun ,
  • Qian Li ,
  • Shi Zefeng
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  • Department of Chemistry, Lishui University, Lishui 323000

Received date: 2011-08-30

  Revised date: 2011-11-03

  Online published: 2012-04-24

Supported by

Project supported by the Natural Science Foundation of Zhejiang Province (No. Y407240) and the Key Science Foundation of Lishui University (No. KZ20H03).

摘要

在无金属催化剂的条件下, 利用微波加热促进C—O, C—N 和C—S 交叉偶联反应. 实验发现以DMSO 为溶剂,t-BuOK 为碱, 利用微波加热, 活化的氯代芳烃能与各类亲核试剂顺利反应, 得到中等及优良的产率.

本文引用格式

袁艳琴 , 郭圣荣 , 莫建军 , 钱利 , 石泽凤 . 无催化剂微波促进下C—O, C—N 和C—S 交叉偶联反应研究[J]. 有机化学, 2012 , 32(04) : 732 -741 . DOI: 10.6023/cjoc1108302

Abstract

A rapid and direct coupling reactions of various N/O/S nucleophilic reagents with aryl halides have been developed in good to high yields under microwave irradiation without a transition-metal catalyst. These reactions are a particularly powerful method for the coupling of electron-withdraw aryl halides with various nucleophilic reagents. A variety of products including aryl ethers, N-arylamides, and aryl thioethers were synthesized in good to excellent yields.

参考文献

[1] For reviews, see: (a) Barchechath, S. D.; Tawatao, R. I.; Corr, M.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 2005, 48, 6409. (b) Zhong, C.; He, J.; Xue, C.; Li, Y. Bioorg. Med. Chem. 2004, 12, 4009. (c) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.  

[2] Xu, H.; Man, Q.; Lin, Y.; Li, Y.; Feng, Y. Chin. J. Org. Chem. 2010, 30(1), 9 (in Chinese). (许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30.)

[3] (a) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. 2007, 46, 934. (b) Chen, Y-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609. (c) Buchwald, S. L.; Altman, R. A. Org. Lett. 2006, 8, 2779. (d) Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.  

[4] (a) Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Organometallics 2007, 26, 65. (b) Ouali, A.; Spindler, J.-F.; Cristau, H. J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499.  

[5] (a) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.  

[6] Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.  

[7] (a) Cristau, H.-J.; Cellier, P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695. (b) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47(17) 3096. (c) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 38(48), 6954. (d) Cristau, H.-J.; Cellier, P. P.; Hamada, S.; Spindler, J.-F.; Taillefer, M. Org. Lett. 2004, 6(6), 913.  

[8] (a) Buchwald, S. L.; Klapars, A.; Huang, X. H. J. Am. Chem. Soc. 2002, 124, 7421. (b) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69(17), 5578.  

[9] (a) Shafir, S.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742. (b) Lv, X.; Bao, W. J. Org. Chem. 2007, 72(10), 3863. (c) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 793. (d) Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490.  

[10] (a) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (b) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809. (c) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164. (d) Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598. (e) Wang, Z.; Bao, W.; Jiang, Y. Chem. Commun. 2005, 2849. (f) Yang, T.; Lin, C.; Fu, H. Org. Lett. 2005, 7, 4781. (g) Deng, W.; Wang, Y. F.; Zhang, C.; Liu, L.; Guo, Q.-X. Chin. Chem. Lett. 2006, 17, 313.

[11] (a) Nilsson, P.; Olofsson, K.; Larhed, M. Top. Curr. Chem. 2006, 266, 103. (b) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250. (c) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107(6), 2563. (d) Appukkuttan, P.; Eycken, E. V. Eur. J. Org. Chem. 2008, 1133. (e) Polshettiwar, V.; Varma, S. Green Chem. 2010, 12, 743. (f) Kelsey, R. S.; Platt, Z. H.; Nguyen, M.; Andrew, W. H. J. Org. Chem. 2008, 73(11), 4291. (g) Xu, G.; Wang. Y.-G. Org. Lett. 2004, 6(6), 985. (h) Chow, W. S.; Chan T. H. Tetrahedron Lett. 2009, 50, 1286. (i) Shi, L.; Wang, M.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515. (j) Wang, X.-Q.; Zhao, Z.-G.; Li, W.-J.; Liu, X.-L.; Han, T. Chin. J. Org. Chem. 2010, 30(5), 764 (in Chinese). (王晓庆, 赵志刚, 李伟杰, 刘兴利, 韩涛, 有机化学, 2010, 30(5), 764.)

[12] Zhu, X.-H.; Chen, G.; Ma, Y.; Song, H.-C.; Xu, Z.-L.; Wan, Y.-Q. Chin. J. Chem. 2007, 25, 546.

[13] Li, F.; Wang, Q.; Ding, Z.; Tao, F. G. Org. Lett. 2003, 5(12), 2169.

[14] Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553.  

[15] Yang, X.-D.; Li, L.; Zhang, H.-B. Helv. Chim. Acta 2008, 91, 1435.  

[16] Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.  

[17] Zhu, D.; Wang, R.; Mao, J.; Xu, L.; Wu, F.; Wan, B. J. Mol. Catal. A: Chem. 2006, 256, 256.  

[18] Sreedhar, B.; Surendra P.; Reddy, M.; Reddy, A. Synthesis 2009, 1732.

[19] Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 640.  

[20] Herrero, M. T.; Martin, R. S.; Dominguez, E. Tetrahedron 2009, 65, 1500.  

[21] Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254.

[22] Zhu, D.; Xu, L.; Wu, F.; Wan, B. Tetrahedron Lett. 2006, 47, 5781.  

[23] Verma, A. K.; Singh J.; Chaudhary, R. Tetrahedron Lett. 2007, 48, 7199.  
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