综述与进展

单质碘促进的有机反应研究进展

  • 赵巾巾 ,
  • 高文超 ,
  • 常宏宏 ,
  • 李兴 ,
  • 刘强 ,
  • 魏文珑
展开
  • 太原理工大学化学化工学院生物与制药工程系 太原 030024

收稿日期: 2014-05-04

  修回日期: 2014-06-02

  网络出版日期: 2014-06-23

基金资助

山西省自然科学基金(Nos. 2012021007-2,2011011010-2)、山西省高等学校科技创新基金(No. 20120006)、太原理工大学引进人才启动经费(No. tyut-rc201307a)资助项目.

Recent Advances in Iodine-Mediated Organic Reactions

  • Zhao Jinjin ,
  • Gao Wenchao ,
  • Chang Honghong ,
  • Li Xing ,
  • Liu Qiang ,
  • Wei Wenlong
Expand
  • College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received date: 2014-05-04

  Revised date: 2014-06-02

  Online published: 2014-06-23

Supported by

Project supported by the Natural Science Foundation of Shanxi Province (Nos. 2012021007-2, 2011011010-2), the Scientific and Technologial Innovation Programs of Higher Education Institutions in Shanxi Province (No. 20120006), and the Qualified Personnel Foundation of Taiyuan University of Technology (No. tyut-rc201307a).

摘要

单质碘作为有机化学中结构最为简单的反应试剂之一,其促进的有机转化在最近几年越来越受到人们的关注.总结了单质碘的氧化性,酸性和亲电性3类基本化学性质,并针对3类性质所涉及的相关反应性报道进行了介绍. 除此之外,还总结了近5年来单质碘作为催化剂在杂环合成,偶联反应,及C—H官能团转化等方面的应用.

本文引用格式

赵巾巾 , 高文超 , 常宏宏 , 李兴 , 刘强 , 魏文珑 . 单质碘促进的有机反应研究进展[J]. 有机化学, 2014 , 34(10) : 1941 -1957 . DOI: 10.6023/cjoc201405003

Abstract

As one of simplest chemical reagents, iodine has promoted diverse organic transformations, which have attracted much attention in recent years. The present review summarizes three basic chemical features of iodine in organic synthesis: the oxidative reactivity, the acidic reactivity and the electrophilic reactivity, along with the introduction of corresponding representative examples. Furthermore, the iodine-catalyzed reactions involed in the synthesis of heterocycles, organic coupling reactions, the C-H functionalization, and other applications are also presented in this review.

参考文献

[1] Swain, P. A. Bull. Hist. Chem. 2005, 30, 103.
[2] (a) Togo, H.; Iida, S. Synlett 2006, 2159.
(b) Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979.
[3] Leal, J. P.; Marques, N.; Takats, J. J. Organomet. Chem. 2001, 632, 209.
[4] Svensson, P. H.; Kloo, L. Chem. Rev. 2003, 103, 1649.
[5] (a) Stanbury J. B. In Endemic Goitre, World Health Organization, Geneva, 1960, pp. 261~262.
(b) Vitamine and mineral requirements in human nutrition. In Iodine, 2nd ed, World Health Organization, Geneva, 2004, pp. 303~304.
[6] (a) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937.
(b) Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Chem. Eur. J. 2012, 18, 5460.
[7] (a) Zhou, Y.; Yan, P.-F.; Li, G.-M.; Chen, Z.-J. Chin. J. Org. Chem. 2009, 29, 1719 (in Chinese).
(周颖, 闫鹏飞, 李光明, 陈正军, 有机化学, 2009, 29, 1719.)
(b) Wang, H.-S.; Miao, J.-Y.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 615 (in Chinese).
(王宏社, 苗建英, 赵立芳, 有机化学, 2005, 25, 615.)
[8] Jereb, M.; Vra?i?, D.; Zupan, M. Tetrahedron 2011, 67, 1355.
[9] Das, S.; Borah, R.; Devi, R. R.; Thakur, A. J. Synlett 2008, 2741.
[10] Ren, Y.-M.; Cai, C.; Yanga, R.-C. RSC Adv. 2013, 3, 7182.
[11] Mphahlele, M. J. Molecules 2009, 14, 5308.
[12] Küpper, F. C.; Feiters, M. C.; Olofsson, B.; Kaiho, T.; Yanagida, S.; Zimmermann, M. B.; Carpenter, L. J.; Luther Ⅲ, G. W.; Lu, Z.; Jonsson, M.; Kloo, L. Angew. Chem., Int. Ed. 2011, 50, 11598.
[13] (a) Yamada, S.; Morizono, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329.
(b) Yamamoto, K.; Shimizu, M.; Yamada, S. J. Org. Chem. 1992, 57, 33.
[14] Mori, N.; Togo, H. Synlett 2005, 1456.
[15] Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70.
[16] Doi, J. T.; Musker, W. K. J. Am. Chem. Soc. 1981, 103, 1159.
[17] (a) Mallory, F. B.; Mallory, C. W. Org. React. 1984, 30, 1.
(b) Yamato, T.; Miyamoto, S.; Hironaka, T.; Miura, Y. Org. Lett. 2005, 7, 3.
[18] Yeh, H.; Yeh, S.; Chen, C. Chem. Commun. 2003, 2632.
[19] (a) Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132, 13226. (b) Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008.(c) Zi, W.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2012, 134, 9126.
(d) Teng, M.; Zi, W.; Ma, D. Angew. Chem., Int. Ed. 2014, 53, 1814.
[20] (a) Zhu, Y.; Liu, M.; Jia, F.; Yuan, J.; Gao, Q.; Lian, M.; Wu, A. Org. Lett. 2012, 14, 3392.
(b) Zhu, Y.; Jia, F.; Liu, M.; Wu, L.; Cai, Q.; Gao, Y.; Wu, A. Org. Lett. 2012, 14, 5378.
(c) Yang, Y.; Gao, M.; Zhang, D.-X.; Wu, L.-M.; Shu, W.-M.; Wu, A.-X. Tetrahedron 2012, 68, 7338.
[21] Gao, Q.; Wu, X.; Liu, S.; Wu, A. Org. Lett. 2014, 16, 1732.
[22] Yin, G.; Zhou, B.; Meng, X.; Wu, A.; Pan, Y. Org. Lett. 2006, 8, 2245.
[23] Zhu, Y.; Fei, Z.; Liu, M.; Jia, F.; Wu, A. Org. Lett. 2013, 15, 378.
[24] Fei, Z.; Zhu, Y.-P.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X. Tetrahedron Lett. 2013, 54, 1222.
[25] Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J.; Wu, A. Org. Lett. 2009, 11, 3810.
[26] (a) Li, Y.-X.; Ji, K.-G.; Wang, H.-X.; Ali, S.; Liang, Y.-M. J. Org. Chem. 2011, 76, 744.
(b) Li, Y.-X.; Wang, H.-X.; Ali, S.; Xia, X.-F.; Liang, Y.-M. Chem. Commun. 2012, 48, 2343.
[27] Wu, W.-B.; Huang, J.-M. Org. Lett. 2012, 14, 5832.
[28] Gao, W.-C.; Jiang, S.; Wang, R.-L.; Zhang, C. Chem. Commun. 2013, 49, 4890.
[29] Yu, W.; Huang, G.; Zhang, Y.; Liu, H.; Dong, L.; Yu, X.; Li, Y.; Chang, J. J. Org. Chem. 2013, 78, 10337.
[30] Sawangphon, T.; Katrun, P.; Chaisiwamongkhol, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C. Synth. Commun. 2013, 43, 1692.
[31] Gao, Q.; Wu, X.; Jia, F.; Liu, M.; Zhu, Y.; Cai, Q.; Wu, A. J. Org. Chem. 2013, 78, 2792.
[32] (a) Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441.
(b) Kotnis, A. S. Tetrahedron Lett. 1990, 31, 481.
[33] Yadav, J. S.; Reddy, B. V. S.; Sabitha, G.; Reddy, G. S. K. K. Synthesis 2000, 1532.
[34] (a) Cruickshank, F. R.; Benson, S. W. J. Phys. Chem. 1969, 73, 733. (b) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed., Wiley, Toronto, 1988.
[35] (a) Prout, C. K.; Wright, J. D. Angew. Chem., Int. Ed. Engl. 1968, 7, 659.
(b) Bent, H. A. Chem. Rev. 1968, 68, 587.
[36] Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Tetrahedron Lett. 2002, 43, 879.
[37] Das, S.; Borah, R.; Devi, R. R.; Thakur, A. J. Synlett 2008, 2741.
[38] Vaino, A. R.; Szarek, W. A. Chem. Commun. 1996, 2351.
[39] (a) Wahlstrom, J. L.; Ronald, R. C. J. Org. Chem. 1998, 63, 6021.
(b) Donohoe, T. J.; Harris, R. M.; Williams, O.; Hargaden, G. C. J. Am. Chem. Soc. 2009, 131, 12854.
[40] Jereb, M.; Vra?i?, D.; Zupan, M. Tetrahedron 2011, 67, 1355.
[41] (a) Lin, X.-F.; Cui, S.-L.; Wang, Y-G. Tetrahedron Lett. 2006, 47, 3127.
(b) Lin, C.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. J. Org. Chem. 2006, 71, 6588.
(c) Li, X.; Mao, Z.; Wang, Y.; Chen, W.; Lin, X. Tetrahedron 2011, 67, 3858.
(d) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 4971.
(e) Lingam, Y.; Rao, D. M.; Bhowmik, D. R.; Santu, P. S.; Rao, K. R.; Slam, A. I. Tetrahedron Lett. 2007, 48, 7243.
(f) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
[42] Lin, X.-F.; Cui, S.-L.; Wang, Y.-G. Teteahedron Lett. 2006, 47, 3127.
[43] Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Tetrahedron 2004, 60, 2051.
[44] Mphahlele, M. J. Molecules 2009, 14, 4814.
[45] Bougault, M. J. C. R. Hebd Seances Acad. Sci. 1904, 139, 864.
[46] Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448.
[47] (a) Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171.
(b) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
(c) Robin, S.; Rousseau, G. Tetrahedron 1998, 54, 13681.
(d) van Tamelen, E. E.; Shamma, M. J. Am. Chem. Soc. 1954, 76, 2315.
(e) Bernett, G.; Doi. J. T.; Musker, W. K. J. Org. Chem. 1985, 50, 2048.
(f) Cuzzupe, A. N.; Di Florio, R.; Rizzacasa, M. A. J. Org. Chem. 2002, 67, 4392.
[48] (a) Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20655.
(b) Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332.
[49] (a) Blot, V.; Reboul, V.; Metzner, P. J. Org. Chem. 2004, 69, 1196.
(b) Murai, T.; Niwa, H.; Kimura, T.; Shibahara, F. Chem. Lett. 2004, 33, 508.
(c) Barks, J. M.; Knight, D. W.; Seaman, C. J.; Weingarten, G. G. Tetrahedron Lett. 1994, 35, 7259.
(d) Jones, A. D.; Knight, D. W. Chem. Commun. 1996, 915.
[50] Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 3942.
[51] (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
(b) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 736.
(c) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 738.
[52] Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
[53] Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
[54] (a) Bew, S. P.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 1007.
(b) El-Tach, G. M.; Evans, A. B.; Knight, D. W.; Jones, S. Tetrahedron Lett. 2001, 42, 5945.
[55] Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles, 2nd ed., Wiley-VCH, Weinheim, 2003, pp. 52~62.
[56] Liu, Y.; Zhou, S. Org. Lett. 2005, 7, 4609.
[57] Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203.
[58] Peng, A. Y.; Ding, Y. X. Org. Lett. 2004, 6, 1119.
[59] Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
[60] Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
[61] Foot, O. F.; Knight, D. W.; Cheng, A.; Low, L.; Li, Y.-F. Tetrahedron Lett. 2007, 48, 647.
[62] Hessian, K. O.; Flynn, B. L. Org. Lett. 2006, 8, 243.
[63] Ali, S.; Zhu, H.; Xia, X. F.; Ji, K. G.; Yang, Y. F.; Song, X. R.; Liang, Y. M. Org. Lett. 2011, 13, 2598.
[64] Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
[65] (a) Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720.
(b) Huo, Z.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2010, 75, 1266.
[66] Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 3651.
[67] (a) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011.
(b) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377.
(c) Ren, X.-F.; Turos, E. Tetrahedron Lett. 1993, 34, 1575.
[68] Kitagawa, O.; Inoue, T.; Hirano, K.; Taguchi, T. J. Org. Chem. 1993, 58, 3106.
[69] Khan, Z. A.; Wirth, T. Org. Lett. 2009, 11, 229.
[70] Zhang, X.; Sarkar, S.; Larock, R. C. J. Org. Chem. 2006, 71, 236.
[71] Fei, N.; Hou, Q.; Wang, S.; Wang, H.; Yao, Z. J. Org. Biomol. Chem. 2010, 8, 4096.
[72] Verma, A. K.; Shukla, S. P.; Singh, J.; Rustagi, V. J. Org. Chem. 2011, 76, 5670.
[73] Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141.
[74] (a) Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2013, 15, 3274.
(b) Chen, C.-C.; Yang, S.-C.; Wu, M.-J. J. Org. Chem. 2011, 76, 10269.
(c) Ferrara, G.; Jin, T. N.; Akhtaruzzaman, M.; Islamc, A.; Han, L. Y.; Jiang, H.; Yamamoto, Y. Tetrahedron Lett. 2012, 53, 1946.
(d) Xie, Y.-X.; Yan, Z.-Y.; Qian, B.; Deng, W.-Y.; Wang, D.-Z.; Wu, L.-Y.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2009, 5451.
[75] Batchu, H.; Bhattacharyya, S.; Batra, S. Org. Lett. 2012, 14, 6330.
[76] Bharathiraja, G.; Sakthivel, S.; Sengoden, M.; Punniyamurthy, T. Org. Lett. 2013, 15, 4996.
[77] Gao, W.-C.; Wang, R.-L.; Zhang, C. Org. Biomol. Chem. 2013, 11, 7123.
[78] Gao, Q.-H.; Fei, Z.; Zhu, Y.-P.; Lian, M.; Jia, F.-C.; Liu, M.-C.; She, N.-F.; Wu, A.-X. Tetrahedron 2013, 69, 22.
[79] (a) Huang, H. W.; Ji, X. C.; Wu, W. Q.; Jiang, H. F. Adv. Synth. Catal. 2013, 355, 170.
(b) Zhao, J.; Huang, H.; Wu, W.; Chen, H.; Jiang, H. Org. Lett. 2013, 15, 2604.
[80] Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092.
[81] (a) Wan, C.; Zhang, J.; Wang, S.; Fan, J.; Wang, Z. Org. Lett. 2010, 12, 2338.
(b) Wan, C.; Gao, L.; Wang, Q.; Zhang, J.; Wang, Z. Org. Lett. 2010, 12, 3902.
[82] (a) Zhang, J. T.; Zhu, D. P.; Yu, C. M.; Wan, C. F.; Wang, Z. Y. Org. Lett. 2010, 12, 2841.
(b) Yan, Y. Z.; Wang, Z. Y. Chem. Commun. 2011, 47, 9513.
[83] Wang, Q.; Wan, C.; Gu, Y.; Zhang, J.; Gao, L.; Wang, Z. Green Chem. 2011, 13, 578.
[84] Yan, Y.; Wang, Z. Chem. Commun. 2011, 47, 9513.
[85] Xu, K.; Hu, Y.; Zhang, S.; Zha, Z.; Wang, Z. Chem. Eur. J. 2012, 18, 9793.
[86] Xiao, F.; Chen, H.; Xie, H.; Chen, S.; Yang, L.; Deng, G.-J. Org. Lett. 2014, 16, 50.
[87] Nobuta, T.; Tada, N.; Fujiya, A.; Kariya, A.; Miura, T.; Itoh, A. Org. Lett. 2013, 15, 574.
[88] Zhu, Y.-P.; Liu, M.-C.; Cai, Q.; Jia, F.-C.; Wu, A.-X. Chem. Eur. J. 2013, 19, 10132.
[89] He, Z.; Liu, W.; Li, Z. Chem. Asian J. 2011, 6, 1340.
[90] Francisco, C. G.; Freire, R.; Herrera, A. J.; Peréz-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1959.
[91] (a) Fan, R.; Pu, D.; Wen, F.; Wu, J. J. Org. Chem. 2007, 72, 8994.
(b) Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2003, 68, 1012.
(c) Katohgi, M.; Togo, H.; Yamaguchi, K.; Yokoyama, M. Tetrahedron 1999, 55, 14885.
(d) Koag, M.; Lee, S. Org. Lett. 2011, 13, 4766.
[92] (a) Donohoe, T. J.; Kabeshov, M. A.; Rathi, A. H.; Smith, I. E. D. Synlett 2010, 2956.
(b) Gao, M.; Yang, Y.; Wu, Y.-D.; Deng, C.; Cao, L.-P.; Meng, X.-G.; Wu, A.-X. Org. Lett. 2010, 12, 1856.
[93] (a) Wang, Z.; Yin, G.; Qin, J.; Gao, M.; Cao, L.; Wu, A. Synthesis 2008, 3675.
(b) Gao, M.; Yin, G.; Wang, Z.; Wu, Y.; Guo, C.; Pan, Y.; Wu, A. Tetrahedron 2009, 65, 6047.
(c) Xue, W.-J; Guo, Y.-Q.; Gao, F.-F.; Li, H.-Z.; Wu, A.-X. Org. Lett. 2013, 15, 890.
(d) Zhu, Y.-P.; Gao, Q.-H.; Lian, M.; Yuan, J.-J.; Liu, M.-C.; Zhao, Q.; Yang, Y.; Wu, A.-X. Chem. Commun. 2011, 47, 12700.
[94] Xu, W.; Kloeckner, U.; Nachtsheim, B. J. J. Org. Chem. 2013, 78, 6065.

文章导航

/