研究简报

钯催化炔酸与烯烃串联碳酯化反应研究

  • 李建晓 ,
  • 张振明 ,
  • 李春生 ,
  • 罗维 ,
  • 杨少容
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  • a 华南理工大学化学与化工学院 广州 510640;
    b 华南理工大学分析测试中心 广州 510640

收稿日期: 2015-05-21

  修回日期: 2015-06-05

  网络出版日期: 2015-06-16

基金资助

国家自然科学基金(Nos. 21102047, 31101221)和中国博士后科学基金(No. 2015M572303)资助项目.

Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes

  • Li Jianxiao ,
  • Zhang Zhenming ,
  • Li Chunsheng ,
  • Luo Wei ,
  • Yang Shaorong
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  • a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
    b Analytical and Testing Center, South China University of Technology, Guangzhou 510640

Received date: 2015-05-21

  Revised date: 2015-06-05

  Online published: 2015-06-16

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221) and the China Postdoctoral Science Foundation (No. 2015M572303).

摘要

室温条件下, 以离子液体为溶剂, 利用炔酸与烯烃衍生物发生串联碳酯化反应, 以中等至优良产率(58%~83%)合成系列官能团化的α-亚甲基-γ-丁内酯衍生物. 其结构均经IR, 1H NMR, 13C NMR及HRMS确证. 该串联反应具有反应条件温和、底物适用范围广、环境友好等优点, 可为具有α-亚甲基-γ-丁内酯骨架的天然产物及复杂药物分子的合成提供简便的途径.

本文引用格式

李建晓 , 张振明 , 李春生 , 罗维 , 杨少容 . 钯催化炔酸与烯烃串联碳酯化反应研究[J]. 有机化学, 2015 , 35(10) : 2199 -2204 . DOI: 10.6023/cjoc201505033

Abstract

An efficient and mild palladium-catalyzed cascade carboesterification has been developed to afford functionalized α-methylene-γ-lactones in moderate to good yields with high regio-and diastereo-selectivities. Their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. Furthermore, this reaction provided a novel and convenient methodology for the construction of naturally occurring biologically active α-methylene-γ-lactones.

参考文献

[1] (a) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981. (b) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
[2] (a) Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202. (b) Hu, M.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 608.
[3] Muniz, K.; Hovelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
[4] Wickens, Z. K.; Guzmán, P. E.; Grubbs, R. H. Angew. Chem., Int. Ed. 2015, 54, 236.
[5] Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321.
[6] Zhang, Z.; Ouyang, L.; Wu, W.; Li, J.; Zhang, Z.; Jiang, H. J. Org. Chem. 2014, 79, 10734.
[7] Hyster, T. K.; Dalton, D. M.; Rovis, T. Chem. Sci. 2015, 6, 254.
[8] Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578.
[9] Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.
[10] Peng, H.; Liu, G. Org. Lett. 2011, 13, 772.
[11] Park, C. P.; Lee, J. H.; Yoo, K. S.; Jung, K. W. Org. Lett. 2010, 12, 2450.
[12] Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426.
[13] Albrecht, A.; Albrecht, ?.; Janecki, T. Eur. J. Org. Chem. 2011, 2747.
[14] (a) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (b) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
[15] Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198.
[16] (a) Huang, L.; Wang, Q.; Liu, X.; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 5696. (b) Zhang, Z.; Wu, W.; Liao, J.; Li, J.; Jiang, H. Chem. Eur. J. 2015, 21, 6708.
[17] (a) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736. (b) Wu, W.; Jiang, H. Acc. Chem. Res. 2014, 47, 2483.
[18] (a) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477. (b) Li, J.; Yang, S. Chin. J. Org. Chem. 2013, 33, 2407 (in Chinese). (李建晓, 杨少容, 有机化学, 2013, 33, 2407.) (c) Yang, S.; Ling, C.; Ma, J.; Zhang, L.; Li, J.; Luo, W. Chin. J. Org. Chem. 2014, 34, 1148 (in Chinese). (杨少容, 凌厂围, 马建业, 张蕾, 李建晓, 罗维, 有机化学, 2014, 34, 1148.) (d) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381. (e) Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sun, Y.; Jiang, H. Angew. Chem. Int. Ed. 2014, 53, 7219. (f) Li, J.; Li, C.; Yang, S.; Luo, W. Chin. J. Org. Chem. 2015, 35, 898 (in Chinese). (李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.) (g) Li, J.; Zhu, Z.; Yang, S.; Zhang, Z.; Wu, W.; Jiang, H. J. Org. Chem. 2015, 80, 3870.
[19] Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765;
[20] Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
[21] Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
[22] Miao, C. X.; He, L. N.; Wang, J. Q.; Wang, J. L. Adv. Synth. Catal. 2009, 351, 2209.

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