单质碘促进的有机反应研究进展

doi:10.6023/cjoc201405003

摘要/Abstract

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.

关键词: 单质碘, 氧化, 酸性, 亲电环化, 杂环合成, 有机催化

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.

Key words: iodine, oxidation, acidity, electrophilic cyclisation, heterocycle syntheses, organocatalysis

引用此文

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.

Zhao Jinjin, Gao Wenchao, Chang Honghong, Li Xing, Liu Qiang, Wei Wenlong. Recent Advances in Iodine-Mediated Organic Reactions[J]. Chin. J. Org. Chem., 2014, 34(10): 1941-1957.

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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.