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2012 >Issue 03: 574 - 579

DOI: https://doi.org/10.6023/cjoc1109062

研究论文

带官能团的双有机碘化锌试剂与酰氯的反应研究

  • 徐长明 ,
  • 杨磊 ,
  • 黄丹凤 ,
  • 牛腾 ,
  • 胡雨来 ,
  • 王克虎
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  • 西北师范大学化学化工学院 兰州 730070

收稿日期: 2011-09-06

  修回日期: 2011-10-27

  网络出版日期: 2012-03-24

基金资助

国家自然科学基金(No. 20472068)、甘肃省自然科学基金(No. 3ZS041-A25-003)、教育部高等学校博士学科点专项科研基金(No. 200807360001)资助项目.

收起

Study on the Coupling Reaction of Fuctionalized Bisorganozinc Iodides and Acyl Chlorides

  • Xu Changming ,
  • Yang Lei ,
  • Huang Danfeng ,
  • Niu Teng ,
  • Hu Yulai ,
  • Wang Kehu
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2011-09-06

  Revised date: 2011-10-27

  Online published: 2012-03-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 2072068), the Natural Science Foundation of Gansu Province (No. 3ZS041-A25-003), and the Specialized Research Fund of the Doctoral Propram of Higher Education (No. 200807360001).

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摘要

探索了带醚键、酯基、羰基的双有机锌试剂的制备及其在CuCN·2LiCl 存在下和酰氯的反应, 得到了带官能团的二酮类化合物. 该方法条件温和, 操作简便, 产率中等, 提供了合成带官能团的长链二酮类化合物的一种简便方法.

关键词： 双有机碘化锌试剂; 酰氯; 二酮类化合物

本文引用格式

徐长明 , 杨磊 , 黄丹凤 , 牛腾 , 胡雨来 , 王克虎 . 带官能团的双有机碘化锌试剂与酰氯的反应研究[J]. 有机化学, 2012 , (03) : 574 -579 . DOI: 10.6023/cjoc1109062

Abstract

This paper investigated the preparation of fuctionalized bisorganozinc iodides with ether, ester, carbonyl groups and the reactions with acyl chlorides in the presence of CuCN?2LiCl generating fuctionalized diketones. The method has the advantages of mild and simple reaction conditions with medium yields, and provides a simple synthesis procedure of fuctionalized long-chain diketone compounds.

Key words： bisorganozinc iodide; acyl chloride; diketone compound

参考文献

[1] Frankland, E. Liebigs Ann. Chem. 1849, 71, 171.

[2] Negishi, E. Acc. Chem. Res. 1982, 15, 340.  

[3] (a) Furstner, A. Synthesis 1989, 571.(b) Knochel, P.; Almeana Perea, J. J.; Jones, P. Tetrahedron 1998,54, 8275.  

[4] Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem.1988, 53, 2390.  

[5] Hunsdiecker, H.; Erlbach, H.; Vogt, E. DE 722467, 1942 [Chem.Abstr. 1943, 37, P 5080].  

[6] Wittig, G.; Jautelat, M. Liebigs. Ann. Chem. 1967, 702, 24.  

[7] (a) Sato, T.; Soai, K.; Suzuki, K.; Mukaiyama, T. Chem. Lett. 1978,601.(b) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J.Am. Chem. Soc. 1979, 101, 1455.  

[8] (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.(b) Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int.Ed. Engl. 1993, 32, 1176.(c) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116,1571.(d) Wang, Y.; Gladysz, J. A. J. Org. Chem. 1995, 60, 903.(e) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama,M. Tetrahedron 1997, 53, 11223.(f) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.(g) Knochel, P.; Vettel, S.; Eisenberg, C. Appl. Organomet. Chem.1995, 9, 175.  

[9] (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc.1980, 102, 3298.(b) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.(c) Negishi, E. Acc. Chem. Res. 1982, 15, 340.(d) Negishi, E.; Bagheri, V.; Chatterjee, S.; Luo, F.-T.; Miller, J. A.;Stoll, A. T. Tetrahedron Lett. 1983, 24, 5181.  

[10] AchyuthaRao, S.; Knochel, P. J. Org. Chem. 1991, 56, 4591.  

[11] (a) Wang, J.-X.; Fu, Y.; Hu, Y. Angew Chem., Int. Ed. 2002, 41,2757.(b) Hu, Y.; Yu, J.; Yang, S.; Wang, J.-X.; Yin, Y. Synlett 1998, 1213.(c) Hu, Y.; Wang, J.-X.; Li, W. Chem. Lett. 2001, 174.(d) Wang, J.-X.; Fu, Y.; Hu, Y.; Wang, K. Synthesis 2003, 1506.(e) Wang, J.-X.; Wang, K.; Zhao, L.; Li, H.; Fu, Y.; Hu, Y. Adv.Synth. Catal. 2006, 348, 1262;(f) Huang, D.; Wang, J.-X. Synlett 2007, 2272.(h) Fu, Y.; Wang, J.-X.; Wang, K.; Hu, Y. Tetrahedron 2008, 64,11124.(g) Wei, Y.-J.; Ren, H.; Wang, J.-X. Tetrahedron Lett. 2008, 49,5697.

[12] Xu, C. M.; Yang, L.; Huang, D. F.; Niu, T.; Hu, Y. L. Chin. J. Org.Chem. 2010, 30, 1240 (in Chinese).(徐长明, 杨磊, 黄丹凤, 牛腾, 胡雨来, 有机化学, 2010, 30,1240.)

[13] (a) Hu, Y. L. Ph.D. Dissertation, Lanzhou Institute of ChemicalPhysics, Chinese Academy of Sciences, Lanzhou, 1998 (inChinese).(胡雨来, 博士论文, 中国科学院兰州化学物理研究所, 兰州,1998.)(b) Hart, H.; Curtis, O. E. J. Am. Chem. Soc. 1956, 78, 112.  

[14] (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem.1988, 53, 2390.(b) Picontin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796.  
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