Progress in Iodine-Mediated Sulfonylation Reactions

doi:10.6023/cjoc201504039

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1848-1860.DOI: 10.6023/cjoc201504039 Previous Articles Next Articles

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碘促进的砜基化反应研究进展

胡飞, 高文超, 常宏宏, 李兴, 魏文珑

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:2015-04-27 修回日期:2015-05-26 发布日期:2015-06-04
通讯作者: 高文超, 常宏宏 E-mail:gaowenchao@tyut.edu.cn;changhonghong@tyut.edu.cn
基金资助:
国家自然科学基金(No. 21206103)、太原理工大学青年基金(No. 2014QN011)资助项目.

Progress in Iodine-Mediated Sulfonylation Reactions

Hu Fei, Gao Wenchao, Chang Honghong, Li Xing, Wei Wenlong

College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received:2015-04-27 Revised:2015-05-26 Published:2015-06-04
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21206103) and the Special/Youth Foundation of Taiyuan University of Technology (2014QN011).

Cite this article

Hu Fei, Gao Wenchao, Chang Honghong, Li Xing, Wei Wenlong. Progress in Iodine-Mediated Sulfonylation Reactions[J]. Chin. J. Org. Chem., 2015, 35(9): 1848-1860.

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[1] Otien, H. J. Antimicrob. Chemother. 1986, 17, 689.
[2] Ma, M.; Cheng, Y.; Xu, Z., Xu, P.; Qu, H.; Fang, Y.; Wen, L. Eur. J. Med. Chem. 2007, 42, 93.
[3] Kunkler, I.; James, N.; Maher, J. Expert Rev. Anti-Infect. Ther. 2004, 4, S37.
[4] Taylor, R. J.; Casy, G. Organic Reactions, John Wiley & Sons, Inc. 2004, 62, 357.
[5] Surprenant, S.; Chan, W. Y.; Berthelette, C. Org. Lett. 2003, 5, 4851.
[6] (a) Liao, C.; Liu, F.; Kannan, K. Environ. Sci. Technol. 2012, 46, 6515. (b) Liao, C.; Liu, F.; Guo, Y.; Moon, H. B.; Nakata, H.; Wu, Q.; Kannan, K. Environ. Sci. Technol. 2012, 46, 9138.
[7] (a) Varma, R. S.; Naicker, K. P. Org. Lett. 1999, 1, 189. (b) Jana, N. K.; Verkade, J. G. Org. Lett. 2003, 5, 3787. (c) Piscitelli, F.; Coluccia, A.; Brancale, A.; La Regina, G.; Sansone, A.; Giordano, C.; Silvestri, R. J. Med. Chem. 2009, 52, 1922.
[8] (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M.; Bernini, R. J. Org. Chem. 2004, 69, 5608. (b) Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Org. Lett. 2004, 6, 2105.
[9] Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014, 12, 9743.
[10] Zhao, J.-J.; Gao, W.-C.; Chang, H.-H; Li, X.; Liu, Q.; Wei, W.-L. Chin. J. Org. Chem. 2014, 34, 1941 (in Chinese).(赵巾巾, 高文超, 常宏宏, 李兴, 刘强, 魏文珑, 有机化学, 2014, 34, 1941.)
[11] Pan, X.; Gao, J.; Liu, J.; Lai, J.; Jiang, H.; Yuan, G. Green Chem. 2015, 17, 1400.
[12] Gao, J.; Pan, X.; Liu, J.; Lai, J.; Chang, L.; Yuan, G. RSC Adv. 2015, 5, 27439.
[13] (a) Riddell, N.; Tam, W. J. Org. Chem. 2006, 71, 1934. (b) Kumar, R.; Kumar, T.; Mobin, S. M.; Nambothiri, I. N. N. J. Org. Chem. 2013, 78, 5073.
[14] Kobayashi, T.; Tanaka, Y.; Ohtani, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1987, 16, 1209.
[15] Wei, W.; Wen, J.; Yang, D.; Jing, H.; You, J.; Wang, H. RSC Adv. 2015, 5, 4416.
[16] (a) Nair,V.; Augustine, A.; George, T. G.; Nair, L. G. Tetrahedron Lett. 2001, 42, 6763. (b) Nair, V.; Augustine, A.; Suja, T. D. Synthesis 2002, 2259.
[17] (a) Katrun, P.; Chiampanichayakul, S.; Korworapan, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C. Eur. J. Org. Chem. 2010, 5633. (b) Sawangphon, T.; Katrun, P.; Chaisiwamongkhol, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C. Synth. Commun. 2013, 43, 1692.
[18] Li, X.; Xu, X.; Shi, X. Tetrahedron Lett. 2013, 54, 3071.
[19] Wei, W.; Wen, J.; Yang, D.; Guo, M.; Wang, Y.; You, J.; Wang, H. Chem. Commun. 2015, 51, 768.
[20] Wen, J.; Wei, W.; Xue, S.; Yang, D.; Lou, Y.; Gao, C.; Wang, H. J. Org. Chem. 2015, 80, 4966.
[21] (a) Sulzer-Mossé, S.; Alexakis, A.; Mareda, J.; Bollot, G.; Bernardinelli, G.; Filinchuk, Y. Chem. Eur. J. 2009, 15, 3204. (b) Zhao, P.; Beaudry, C. M. Org. Lett. 2013, 15, 402. (c) Dol, F.; Schaeffer, P.; Lamarche, I.; Mares, A.; Chatelain, P.; Herbert, J. Eur. J. Pharmacol. 1995, 280, 135.
[22] Liu, L. K.; Chi, Y.; Jen, K. Y. J. Org. Chem. 1980, 45, 406.
[23] Inomata, K.; Sasaoka, S. I.; Kobayashi, T.; Tanaka, Y.; Igarashi, S.; Ohtani, T.; Kotake, H. Bull. Chem. Soc. Jpn. 1987, 60, 1767.
[24] (a) Níjera, C.; Baldo, B.; Yus, M. J. Chem. Soc. Perkin Trans. 1988, 1029. (b) Níjera, C.; Sansano, J. M.; Yus, M. J. Chem. Educ. 1995, 72, 664. (c) Caturla, F.; Níjera, C. Tetrahedron 1997, 53, 11449.
[25] Zhang, N.; Yang, D.; Wei, W.; Yuan, L.; Gao, Y.; Wang, H. RSC Adv. 2015, 5, 37013.
[26] Luo, Y. -C.; Pan, X.-J.; Yuan, G.-Q. Tetrahedron 2015, 71, 2119.
[27] Wolff, R. R.; Basava, V.; Giuliano, R. M.; Boyko, W. J.; Schauble, J. H. Can. J. Chem. 2006, 84, 667.
[28] Das, B.; Lingaiah, M.; Damodar, K.; Bhunia, N. Synthesis 2011, 2941.
[29] Tang, S.; Wu, Y.; Liao, W.; Bai, R.; Liu, C.; Lei, A. Chem. Commun. 2014, 50, 4496.
[30] Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao, Y. R.; Li, Y. Y.; Guo, C. C. J. Org. Chem. 2014, 79, 7372.
[31] Gao, X.; Pan, X.; Gao, J.; Huang, H.; Yuan, G.; Li, Y. Chem. Commun. 2015, 51, 210.
[32] (a) Kocienski, P. J. Tetrahedron Lett. 1979, 20, 2649. (b) Grigg, R.; Níjera, C.; Sansano, J. M.; Yus, M. Synth. Commun. 1997, 27, 1111.
[33] (a) Donohoe, T. J.; Kabeshov, M. A.; Rathi, A. H.; Smith, I. E. D. Synlett 2010, 2956. (b) Samakkanad, N.; Katrun, P.; Techajaroonjit, T.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.; Kuhakarn, C. Synthesis 2012, 44, 1693.
[34] (a) Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240. (b) Li, X.; Xu X.; Tang,Y. Org. Biomol. Chem. 2013, 11, 1739.
[35] (a) Mai, W.-P.; Wang, J.-T.; Yang, L.-R.; Yuan, J.-W.; Mao, P.; Xiao, Y.-M.; Qu, L.-B. Chin. J. Org. Chem. 2014, 34, 1958 (in Chinese).(买文鹏, 王继涛, 杨亮茹, 袁金伟, 毛璞, 肖咏梅, 屈凌波, 有机化学, 2014, 34, 1958.)(b) Song, R. J.; Liu, Y.; Xie, Y. X.; Li, J. H. Synthesis 2015, 47, 1195.
[36] Li, X.; Xu, X.; Hu, P.; Xiao, X.; Zhou, C. J. Org. Chem. 2013, 78, 7343.
[37] (a) Zhang, M.; Xie, P.; Zhao, W.; Niu, B.; Wu, W.; Bian, Z.; Pittman, Jr. C. U.; Zhou, A. J. Org. Chem. 2015, 80, 4176. (b) Yu, W. B.; Hu, P.; Fan, Y. ; Yu, C.; Yan, X.; Li, X.; Xu, X. Org. Biomol. Chem. 2015, 13, 3308.
[38] (a) Cazorla, O.; Lacampagne, A.; Fauconnier, J.; Vassort, G. Br. J. Pharmacol. 2003, 139, 99. (b) Dol, F.; Schaeffer, P.; Lamarche, I.; Mares, A.; Chatelain, P.; Herbert, J. Eur. J. Pharmacol. 1995, 280, 135.
[39] (a) Broggini, G.; Diliddo, D.; Zecchi, G. J. Heterocycl. Chem. 1991, 28, 89. (b) Singh, D.; Singh, P. R.; Samant, S. D. Tetrahedron Lett. 2004, 45, 9079.
[40] Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702.
[41] (a) Xiao, F.; Chen, H.; Xie, H.; Chen, S.; Yang, L.; Deng, G. J. Org. Lett. 2013, 16, 50. (b) Katrun, P.; Mueangkaew, C.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2014, 79, 1778.
[42] Zhang, J.; Shao, Y.; Wang, H.; Luo, Q.; Chen, J.; Xu, D.; Wan, X. Org. Lett. 2014, 16, 3312.
[43] Qiu, J. K.; Hao, W. J.; Wang, D. C.; Wei, P.; Sun, J.; Jiang, B.; Tu, S. J. Chem. Commun. 2014, 50, 14782.
[44] Alemín, J.; Marcos, V.; Marzo, L.; Ruano, J. L. G. Eur. J. Org. Chem. 2010, 23, 4482.
[45] Reddy, M. V. R.; Reddy, S. Acta Chim. Hung. 1984, 115, 269.
[46] Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238.
[47] (a) Curti, C.; Laget, M.; Carle, A. O.; Gellis, A.; Vanelle, P. Eur. J. Med. Chem. 2007, 42, 880. (b) Eweas, A. F.; Allam, G.; Abuelsaad, A. S.; ALGhamdi, A. H.; Maghrabi, I. A. Bioorg. Chem. 2013, 46, 17.
[48] Xie, Y. Y.; Chen, Z. C. Synth. Commun. 2001, 31, 3145.
[49] Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
[50] Rawat, V. S.; Reddy, P. L.; Sreedhar, B. RSC Adv. 2014, 4, 5165.
[51] Jeyachandran, M.; Ramesh, P. Org. Chem. Int. 2011, Article ID 360810.
[52] Gao, W.-C.; Zhao, J.-J.; Chang, H.-H.; Li, X.; Liu, Q.; Wei, W.-L. RSC Adv. 2014, 4, 49329.
[53] Gao, W.-C.; Zhao, J.-J.; Hu, F.; Chang, H.-H; Li, X.; Liu, Q.; Wei, W.-L. RSC Adv. 2015, 5, 25222.
[54] Xiao, F.; Chen, S.; Chen, Y.; Huang, H.; Deng, G. J. Chem. Commun. 2015, 51, 652.

碘促进的砜基化反应研究进展

Progress in Iodine-Mediated Sulfonylation Reactions

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