SIOC English
有机化学
高级检索

有机化学 >

2018 , Vol. 38 >Issue 1: 62 - 74

DOI: https://doi.org/10.6023/cjoc201708023

综述与进展

磷自由基对不饱和键的双官能化反应的研究进展

  • 高玉珍 ,
  • 唐果 ,
  • 赵玉芬
展开
  • a 厦门大学化学化工学院 福建省化学生物学重点实验室 厦门 361005;
    b 中国科学院福建物质结构研究所 煤制乙二醇及相关技术重点实验室 福州 350002

收稿日期: 2017-08-11

  修回日期: 2017-08-31

  网络出版日期: 2017-09-08

基金资助

国家自然科学基金（Nos.21232005，21375113）、重点基础研究发展计划（No.2013CB910700）、中央高校基本科研业务费（No.20720160030）、博士后创新人才支持计划（No.BX201700244）资助项目.

收起

Recent Advances of Phosphorus-Centered Radical Promoted Difunctionalization of Unsaturated Carbon-Carbon Bonds

  • Gao Yuzhen ,
  • Tang Guo ,
  • Zhao Yufen
Expand
  • a Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005;
    b Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002

Received date: 2017-08-11

  Revised date: 2017-08-31

  Online published: 2017-09-08

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21232005, 21375113), the National Basic Research Program of China (No. 2013CB910700), the Fundamental Research Funds for the Central Universities (No. 20720160030), the National Postdoctoral Program for Innovative Talents (No. BX201700244).

Fold

摘要

有机膦化合物在有机反应、光电材料、阻燃材料以及药物化学等研究领域都具有广泛的用途，因而探索更高效、更绿色的方法实现有机膦化合物的合成是有机膦化学工作者的主要目标之一.通过磷自由基与不饱和化合物的双官能团化反应可以在一步反应中实现含磷杂环以及多环化合物的构建.按磷自由基引发方式的不同，对近年来磷自由基与不饱和化合物的双官能团化反应的研究进展进行了综述.

关键词： 磷自由基; 双官能团化; 不饱和化合物

本文引用格式

高玉珍 , 唐果 , 赵玉芬 . 磷自由基对不饱和键的双官能化反应的研究进展[J]. 有机化学, 2018 , 38(1) : 62 -74 . DOI: 10.6023/cjoc201708023

Abstract

The scientists have been working on developing more efficient and green ways to synthesize organophosphorus compounds as they have broad utilities such as reagents for chemical reactions, photovoltaic materials, flame retardants, biologically active molecules and so on. The difunctionalization reactions between P-center radicals and unsaturated compounds provide powerful methods for the synthesis of organophosphorus compounds in least and concise steps. This review will summarize the recent development in this area on the basis of different types of P-centered radical initiators.

Key words： phosphorus-centered radical; difunctionalization; unsaturated compounds

参考文献

[1] (a) De Clercq, E. Med. Res. Rev. 2011, 31, 118.
(b) Queffélec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777.
(c) Zhao, Y.; Xiao, Q.; Ju, Y.; Li, Y. Chin. J. Org. Chem. 2001, 21, 869(in Chinese).(赵玉芬, 肖强, 巨勇, 李艳梅, 有机化学, 2001, 21, 869.)
(d) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
[2] (a) Tappe, F. M. J.; Trepohl, V. T.; Oestreich, M. Synthesis 2010, 3037.
(b) Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981.
(c) Shao, C.; Xu, W.; Li, L.; Zhang, X. Chin. J. Org. Chem. 2017, 37, 335(in Chinese).(邵长伟, 徐炜刚, 李亮, 张兴华, 有机化学, 2017, 37, 335.)
(d) Yang, J.; Xiao, J.; Zhou, Y.; Chen, T.; Yin, S.; Han, L. Chin. J. Org. Chem. 2017, 37, 1055(in Chinese).(杨佳, 肖晶, 周永波, 陈铁桥, 尹双凤, 韩立彪, 有机化学, 2017, 37, 1055.)
[3] For selected reviews on reactions involving P-center radical, see:(a) Pan, X.-Q.; Zou, J.-P.; Yi, W.-B.; Zhang, W. Tetrahedron 2015, 71, 7481.
(b) Gao, Y.; Tang, G.; Zhao, Y. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 589.
(c) Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858.
[4] (a) Parsons, A. F.; Sharp, D. J.; Taylor, P. Synlett 2005, 2981.
(b) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Eur. J. Org. Chem. 2006, 1547.
[5] Hirai, T.; Han, L.-B. Org. Lett. 2007, 9, 53.
[6] Mondal, M.; Bora, U. RSC Adv. 2013, 3, 18716.
[7] Pan, X.-Q.; Zou, J.-P.; Zhang, G.-L.; Zhang, W. Chem. Commun. 2010, 46, 1721.
[8] Zhou, J.; Zhang, G.-L.; Zou, J.-P.; Zhang, W. Eur. J. Org. Chem. 2011, 3412.
[9] Li, D.-P.; Pan, X.-Q.; An, L.-T.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2014, 79, 1850.
[10] Pan, X.-Q.; Wang, L.; Zou, J.-P.; Zhang, W. Chem. Commun. 2011, 47, 7875.
[11] Gao, Y.; Wu, J.; Xu, J.; Zhang, P.; Tang, G.; Zhao,Y. RSC Adv. 2014, 4, 51776.
[12] Zhou, S.-F.; Li, D.-P.; Liu, K.; Zou, J.-P.; Asekun, O. T. J. Org. Chem. 2015, 80, 1214.
[13] Xu, J.; Li, X.; Gao, Y.; Zhang, L.; Chen, W.; Fang, H.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 51, 11240.
[14] Gao, Y.; Li, X.; Xu, J.; Wu, Y.; Chen, W.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 51, 1605.
[15] Gao, Y.; Li, X.; Chen, W.; Tang, G.; Zhao, Y. J. Org. Chem. 2015, 80, 11398.
[16] (a) Gao, Y.; Wu, J.; Xu, J.; Wang, X.; Tang, G.; Zhao, Y. Asian J. Org. Chem. 2014, 3, 691.
(b) Li, Y.; Qiu, G.; Ding, Q.; Wu, J. Tetrahedron 2014, 70, 4652.
(c) Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.
(d) Cao, J.-J.; Zhu, T.-H.; Gu, Z.-Y.; Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2014, 70, 6985.
(e) Li, C.-X.; Tu, D.-S.; Yao, R.; Yan, H.; Lu, C.-S. Org. Lett. 2016, 18, 4928.
[17] Zhang, C.; Li, Z.; Zhu, L.; Yu, L.; Wang, Z.; Li, C. J. Am. Chem. Soc. 2013, 135, 14082.
[18] Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.
[19] Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991.
[20] Zhang, H.; Gu, Z.; Li, Z.; Pan, C.; Li, W.; Hu, H.; Zhu, C. J. Org. Chem. 2016, 81, 2122.
[21] Zheng, J.; Zhang, Y.; Wang, D.; Cui, S. Org. Lett. 2016, 18, 1768.
[22] Kong, W.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2014, 53, 5078.
[23] Zhao, J.; Li, P.; Li, X.; Xia, C.; Li, F. Chem. Commun. 2016, 52, 3661.
[24] Wang, N.; Li, L.; Li, Z.-L.; Yang, N.-Y.; Guo, Z.; Zhang, H.-X.; Liu, X.-Y. Org. Lett. 2016, 18, 6026.
[25] Liu, J.; Zhao, S.; Song, W.; Li, R.; Guo, X.; Zhuo, K.; Yue,Y. Adv. Synth. Catal. 2017, 359, 609.
[26] Xu, J.; Yu, X.; Song, Q. Org. Lett. 2017, 19, 980.
[27] Chen, S.; Zhang, P.; Shu, W.; Gao, Y.; Tang, G.; Zhao, Y. Org. Lett. 2016, 18, 5712.
[28] Zhang, H.; Li, W.; Zhu, C. J. Org. Chem. 2017, 82, 2199.
[29] Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Wu, X.-X.; Xu, P.-F.; Liang, Y.-M. Org. Lett. 2016, 18, 216.
[30] Gao, Y.; Lu, G.; Zhang, P.; Zhang, L.; Tang, G.; Zhao, Y. Org. Lett. 2016, 18, 1242.
[31] Zhu, X.-T.; Zhao, Q.; Liu, F.; Wang, A.-F.; Cai, P.-J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2017, 53, 6828.
[32] Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356.
[33] Wang, L.-J.; Wang, A.-Q.; Xia, Y.; Wu, X.-X.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2014, 50, 13998.
[34] Zhou, Z.-Z.; Zheng, L.; Yan, X.-B.; Jin, D.-P.; He. Y.-T.; Liang, Y.-M. Org. Biomol. Chem. 2016, 14, 4507.
[35] Zhou, Z.-Z.; Jin, D.-P.; Li, L.-H.; He, Y.-T.; Zhou, P.-X.; Yan, X.-B.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 5616.
[36] (a) Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed., 2013, 52, 12975.
(b) Chen, Y.-R.; Duan, W.-L. J. Am. Chem. Soc. 2013, 135, 16754.
(c) Zhang, P.; Gao, Y.; Zhang, L.; Li, Z.; Liu, Y.; Tang, G.; Zhao, Y. Adv. Synth. Catal. 2016, 358, 138.
(d) Ma, D.; Chen, W.; Hu, G.; Zhang, Y.; Gao, Y.; Yin, Y.; Zhao, Y. Green Chem. 2016, 18, 3522.
(e) Quint, V.; Morlet-Savary, F.; Lohier, J.-F.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. J. Am. Chem. Soc. 2016, 138, 7436.
[37] Hu, G.; Zhang, Y.; Su, J.; Li, Z.; Gao, Y.; Zhao, Y. Org. Biomol. Chem. 2015, 13, 8221.
[38] Wei, W.; Ji, J.-X. Angew. Chem., Int. Ed. 2011, 50, 9097.
[39] Zhou, Y.; Zhou, M.; Chen, M.; Su, J.; Du, J.; Song, Q. RSC Adv. 2015, 5, 103977.
[40] Zhou, Y.; Rao, C.; Mai, S.; Song, Q. J. Org. Chem. 2016, 81, 2027.
[41] (a) Zhou, M.; Chen, M.; Zhou, Y.; Yang, K.; Su, J.; Du, J.; Song, Q. Org. Lett. 2015, 17, 1786.
(b) Yi, N.; Wang, R.; Zou, H.; He, W.; Fu, W.; He, W. J. Org. Chem. 2015, 80, 5023.
(c) Zhang, P.; Zhang, L.; Gao, Y.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 51, 7839.
(d) Chen, X.; Li, X.; Chen, X.-L.; Qu, L.-B.; Chen, J.-Y.; Sun, K.; Liu, Z.-D.; Bi, W.-Z.; Xia, Y.-Y.; Wu, H.-T.; Zhao, Y.-F. Chem. Commun. 2015, 51, 3846.
[42] Taniguchi, T.; Idota, A.; Yokoyama, S.; Ishibashi, H. Tetrahedron Lett. 2011, 52, 4768.
[43] Zhang, H.-Y.; Mao, L.-L.; Yang, B.; Yang, S.-D. Chem. Commun. 2015, 51, 4101.
[44] Li, Y.-M.; Wang, S.-S.; Yu, F.; Shen, Y.; Chang, K.-J. Org. Biomol. Chem. 2015, 13, 5376.
[45] Wu, J.; Gao, Y.; Zhao, X.; Zhang, L.; Chen, W.; Tang, G.; Zhao, Y. RSC Adv. 2016, 6, 303.
[46] Zhu, Y.-L.; Wang, D.-C.; Jiang, B.; Hao, W.-J.; Wei, P.; Wang, A.-F.; Qiu, J.-K.; Tu, S.-J. Org. Chem. Front. 2016, 3, 385.
[47] Liu, C.; Zhu, M.; Wei, W.; Yang, D.; Cui, H.; Liu, X.; Wang, H. Org. Chem. Front. 2015, 2, 1356.
[48] Zhang, P.; Zhang, L.; Gao, Y.; Tang, G.; Zhao, Y. RSC Adv. 2016, 6, 60922.
[49] (a) Dondoni, A.; Staderini, S.; Marra, A. Eur. J. Org. Chem. 2013, 5370.
(b) Oparina, L. A.; Malysheva, S. F.; Gusarova, N. K.; Belogorlova, N. A.; Vysotskaya, O. V.; Stepanov, A. V.; Albanov, A. I.; Trofimov, B. A. Synthesis 2009, 3427.
(c) Daeffler, C. S.; Grubbs, R. H. Org. Lett. 2011, 13, 6429.
[50] (a) Peng, P.; Peng, L.; Wang, G.; Wang, F.; Luo, Y.; Lei, A. Org. Chem. Front. 2016, 3, 749.
(b) Luo, K.; Chen, Y.-Z.; Yang, W.-C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
[51] Liu, D.; Chen, J.-Q.; Wang, X.-Z.; Xu, P.-F. Adv. Synth. Catal. 2017, 359, 2773.
[52] (a) Johnston, C. P.; Smith, R. T.; Allmendinger, S.; MacMillan, D. W. C. Nature 2016, 536, 322.
(b) Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl, S. S.; Liu, G. Science 2016, 353, 1014.

Options
文章导航

/

〈 〉