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化学进展 2016, Vol. 28 Issue (2/3): 317-327 DOI: 10.7536/PC150819 前一篇   后一篇

• 综述与评论 •

芳基末端炔的合成

雷朋飞1, 张文生2, 匡春香3, 江玉波1*   

  1. 1. 昆明理工大学理学院 昆明 650500;
    2. 焦作师范高等专科学校理工学院 焦作 454001;
    3. 同济大学化学系 上海 200092
  • 收稿日期:2015-08-01 修回日期:2015-09-01 出版日期:2016-03-15 发布日期:2016-01-07
  • 通讯作者: 江玉波 E-mail:ybjiang@kmust.edu.cn
  • 基金资助:
    国家自然科学基金项目(No.21262020)资助
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Synthesis of Terminal Arylacetylenes

Lei Pengfei1, Zhang Wensheng2, Kuang Chunxiang3, Jiang Yubo1*   

  1. 1. Faculty of Science, Kunming University of Science and Technology, Kunming 650500, China;
    2. School of Science and Technology, Jiaozuo Teachers'College, Jiaozuo 454001, China;
    3. Department of Chemistry, Tongji University, Shanghai 200092, China
  • Received:2015-08-01 Revised:2015-09-01 Online:2016-03-15 Published:2016-01-07
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21262020).
芳基末端炔是一类重要的有机合成中间体,在众多领域具有广泛的应用,其合成备受广大研究者的高度关注。本文阐述了末端炔的合成研究进展,着重综述了近十年来芳基末端炔合成发展情况,包括分别以卤代烯烃、卤代芳烃、芳醛等为原料的末端炔的合成方法。文章还对一些方法的应用做了介绍,并对重要反应机理作了分析,最后对该类化合物的合成情况进行了总结并展望了未来发展方向。
关键词： 芳基末端炔, 溴代烯烃, 芳卤, 芳醛
As a kind of important organic synthesis intermediates, terminal arylacetylenes are widely used in many fields and concerned by many researchers. This review mainly describes the synthesis of terminal arylacetylenes by using vinyl bromides, aryl halideas, aromatic aldehyde as the starting materials in recent ten years. The applications and mechanisms of some reactions are also described. The further work needed to do and the development trends in this field are proposed.

Contents
1 Introduction
2 Synthesis of terminal arylacetylenes
2.1 From vinyl halides
2.2 From aryl halides
2.3 From aromatic aldehydes
2.4 Other methods
3 Conclusion

Key words: terminal arylacetylenes, vinyl bromides, aryl halides, aromatic aldehydes

中图分类号: 

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[1] Kanki K, Masuda T. Macromolecules, 2003, 36:1500.
[2] Portenkirchner E, Schlager S, Apaydin D, Oppelt K, Himmelsbach M, Egbe D A M, Neugebauer H, Knor G, Yoshida T, Sariciftci N S. Electrocatalysis, 2015, 6(2):185.
[3] Yang H S, Jin Y H, Du Y, Zhang W. J. Mater. Chem. A, 2014, 2:5986.
[4] Johnson D.G, Lynam J M, Mistry N S, Slattery J M, Thatcher R J, Whitwood A C. J. Am. Chem. Soc., 2013, 135:2222.
[5] Zavesky B P, Babij N R, Wolfe J P. Org. Lett., 2014, 16:4952.
[6] Leventis N, Rawashdeh A M M, Elder I A, Yang J H, Dass A, Chariklia S L. Chem. Mater., 2004, 16:1493.
[7] Otsuka I, Hongo T, Nakade H, Narumi A, Sakai R, Satoh T, Kaga H, Kakuchi T. Macromolecules, 2007, 40:8930.
[8] Zhang H Y, Song J X, Deng J P. Macromol. Rapid. Comm., 2014, 35:1216.
[9] Zhang H Y, Yang W T, Deng J P. J Polym. Sci. Pol. Chem., 2015, 53:1816.
[10] Saeed I, Shiotsuki M, Masuda T. Macromolecules, 2006, 39:5347.
[11] Xu H P, Jin J K, Mao Y, Sun J Z, Yang F, Yuan W Z, Dong Y Q, Wang M, Tang B Z. Macromolecules, 2008, 41:3874.
[12] Onishi N, Shiotsuki M, Masuda T, Sano N, Sanda F. Organometallics, 2013, 32:846.
[13] 江玉波(Jiang Y B), 匡春香(Kuang C X). 化学进展(Progress in Chemistry), 2012, 24(10):1983.
[14] Jung J H, Lim Y G, Lee K H, Koo B T. Tetrahedron Lett., 2007, 48:6442.
[15] Kawamichi T, Inokuma Y, Kawano M, Fujita M. Angew. Chem. Int. Ed., 2010, 49:2375.
[16] Wang C F, Makila E M, Bonduelle C, Rytkonen J, Raula J, Almeida S, Narvanen A, Salonen J J, Lecommandoux S, Hirvonen J T, Santos H A. ACS. Appl. Mater. Interfaces, 2015, 7(3):2006.
[17] Kantheti S, Narayan R, Raju K V S N. RSC Adv., 2015, 5:3687.
[18] Wang Z J, Gao Y, Hou Y L, Zhang C, Yu S J, Bian Q, Li Z M, Zhao W G. Eur. J. Med. Chem., 2014, 86:87.
[19] Chen Y B, Xiao Y X, Shao X S, Xu X Y, Li Z. Chin. J. Chem., 2014, 32:592.
[20] Nguyen T M, Manohar N, Nicewicz D A. Angew. Chem. Int. Ed., 2014,53:6198.
[21] Vaughn T. H. J. Am. Soc. Chem., 1934, 56:2064.
[22] Mieczyslaw M, Alexey A C. Tetrahedron Lett., 2002, 58:7295.
[23] Kuang C X, Yang Q, Senboku H, Tokuda M. Tetrahedron, 2005, 61:4043.
[24] Cheng X Z, Jia J, Kuang C X. Chin. J. Chem., 2011, 29:2350.
[25] Sanaa S K, Sachin U S, Yoel S. Tetrahedron Lett., 2012, 53:2295.
[26] Gronheid R, Zuilhof H, Hellings M G, Cornelisse J, Lodder G. J. Org. Chem., 2003, 68:3205.
[27] Azzena U, Pittalis M, Dettori G, Pisano L, Azara E. J. Organomet. Chem., 2007, 692:3892.
[28] Taillefer M, Ouali A, Renard B, Spindler J F. Chem. Eur. J., 2006, 12:5301.
[29] Masaru O, Yuji M. J. Org. Chem., 2009, 74:442.
[30] Zhao M, Kuang C X, Yang Q, Cheng X Z. Tetrahedron Lett., 2011, 52:992.
[31] Li S H, Chen X B, Hu Y W, Yuan L P, Chen S H, Wu P, Wang W, Zhang S L, Zhang W. Adv. Synth. Catal., 2015, 357:553.
[32] Negishi E, KoTora M, Xu C D. J. Org. Chem., 1997, 62:8957.
[33] Vasilevsky S F, Klyatskaya S V, Elguero J. Tetrahedron Lett., 2004, 60:6685.
[34] Richardson C, Reed C A. J. Org. Chem., 2007, 72:4750.
[35] Gorl C, Alt H G. J. Organomet. Chem., 2007, 692:4580.
[36] Pauly A C, Theato P. J. Polym. Sci. Pol. Chem., 2011, 49:211.
[37] Prasad C K, Raju P V S M. J. Appl. Chem., 2014, 3:1460.
[38] Gehringer M, Forster M, Laufer S A. ACS Comb. Sci., 2015, 17:5.
[39] Li Z A, Wu W B, Qiu G F, Yu G, Liu Y Q, Ye C, Qiu J G, Li Z. J. Polym. Sci. Pol. Chem., 2011, 49:1977.
[40] Wang Y, Huang B, Sheng S R, Cai M Z. J. Chem. Res., 2007, 12:728.
[41] Hao W Y, Wang Y, Sheng S R, Cai M Z. J. Chem. Res., 2008, 11:615.
[42] Xu Y P, Hu R H, Cai M Z. Chin. Chem. Lett., 2008, 19:783.
[43] Kyungho P, Thiruvengadam P, Ayoung P, Sunwoo L. Tetrahedron Lett., 2012, 53:733.
[44] Li J, Huang P C. Beilstein J. Org. Chem., 2011, 7:426.
[45] Corey E J, Fuchs P L. Tetrahedron Lett., 1972, 36:3769.
[46] Hijfte L V, Kolb M, Wite P. Tetrahedron Lett., 1989, 28:3655.
[47] Carran J, Waschbusch R, Marinetti A, Savignac P. Synthesis, 1996, (12):1494.
[48] Beshai M, Dhudshia B, Mills R, Thadani A N. Tetrahedron Lett., 2008, 49:6794.
[49] Li P F, Chen C F. J. Org. Chem., 2012, 77:9250.
[50] Yempala T, Sridevi J P, Yogeeswari P, Sriram D, Kantevari S. Eur. J. Med. Chem., 2014, 71:160.
[51] Wang Z, Campagna S, Yang K H, Xu G Y, Pierce M E, Fortunak J M, Confalone P N. J. Org. Chem., 2000, 65:1889.
[52] Illa O, Bagan X, Cazorla A M, Lyon C, Baceiredo A, Branchadeu V, Ortuno R M. J. Org. Chem., 2006, 71:5320.
[53] Quesada E, Taylor R J K. Tetrahedron Lett., 2005, 46:6473.
[54] Huang K W, Grill D C, Han J H, Szalda D J, Fujita E. Inorg. Chim. Acta, 2008, 361:3327.
[55] Aitken R A, Seth S. Synlett, 1990, 4:211.
[56] Katritzky A R, Wang J, Karodia N, Li J Q. J. Org. Chem., 1997, 62:4142.
[57] Mao S, Gao Y R, Zhu X Q, Guo D D, Wang Y Q. Org. Lett., 2015, 17:1692.
[58] Bejot R, Tisserand S, Li D R, Falck J R, Mioskowski C. Tetrahedron Lett., 2007, 48:3855.
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摘要

芳基末端炔的合成