Recent Advances in the Application of in-situ Generated Hypervalent Iodine Reagents in Organic Synthesis

doi:10.6023/cjoc201906023

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 28-39.DOI: 10.6023/cjoc201906023 Previous Articles Next Articles

原位生成的高价碘试剂在有机合成中的应用进展

杨柳^a, 许国贺^a, 马晶军^a, 杨倩^b, 冯安^a, 崔景港^a

a 河北农业大学渤海校区理工学院河北黄骅 061100;
b 河北农业大学动物医学院河北保定 071000

收稿日期:2019-06-19 修回日期:2019-08-27 发布日期:2019-09-12
通讯作者: 马晶军 E-mail:mjjwjpmartin@163.com
基金资助:
河北省高等学校青年拔尖人才计划（No.BJ201702）和河北农业大学引进博士专项（No.ZD2016027）资助项目.

Recent Advances in the Application of in-situ Generated Hypervalent Iodine Reagents in Organic Synthesis

Yang Liu^a, Xu Guohe^a, Ma Jingjun^a, Yang Qian^b, Feng An^a, Cui Jinggang^a

a College of Science & Technoloy, Agricultural University of Hebei Bohai Campus, Huanghua, Hebei 061100;
b College of Veterinary Medicine, Hebei Agricultural University, Baoding, Hebei 071001

Received:2019-06-19 Revised:2019-08-27 Published:2019-09-12
Supported by:
Project supported by the Young Tip-Top Talents Plan of Universities and Colleges in Hebei Province (No. BJ201702), and the Specific Foundation for Doctor in Hebei Agriculture University of China (No. ZD2016027).

Based on the atomic economy, mild performance and environment friendly, the in-situ generation of hypervalent iodine reagents has been vastly applied in many significant oxidative reactions and asymmetric catalysis. In this paper, the progress of in-situ generated hypervalent iodine reagents is systematically reviewed, including conception and mechanisms. According to the different reaction types, the application of in-situ generated hapervalent iodine reagent in organic synthesis reaction is summarized, including trivalent iodine reagent, pentavalent iodine reagent and chiral hypervalent iodine reagent. The problem of in-situ generated hapervalent iodine researches is analyzed, and the future development of in-situ hapervalent iodine is prospected.

Key words: in-situ generation, hypervalent iodine reagent, organic synthesis

Cite this article

Yang Liu, Xu Guohe, Ma Jingjun, Yang Qian, Feng An, Cui Jinggang. Recent Advances in the Application of in-situ Generated Hypervalent Iodine Reagents in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 28-39.

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References

[1] Musher, J. I. Angew. Chem. Int. Ed. 1969, 8, 54.
[2] (a) Sandin, R. B. Chem. Rev. 1943, 32, 249.
(b) Banks, D. F. Chem. Rev. 1966, 66, 243.
(c) Varvoglis, A. Tetrahedron 1997, 53, 1179.
(d) Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111.
(e) Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094.
(f) Mu, X.; Wu, T.; Wang, H.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878.
(g) Duan, X.; Yang, K.; Wang, Z.; Zhang, L.; Tong, Y.; Liu, H.; Du, K.; Tang, R. Chin. J. Org. Chem. 2015, 35, 2552(in Chinese). (段希焱, 杨坤, 王志成, 张璐, 佟悦, 刘浩哲, 杜珂, 唐榕泽, 有机化学, 2015, 35, 2552.)
[3] (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
(b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
(c) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
(d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
(e) Zhdankin, V. V. ARKIVOC 2009, i, 1.
(f) Kuepper, F. C.; Feiters, M. C.; Olofsson, B.; Kaiho, T.; Yanagida, S.; Zimmermann, M. B.; Carpenter, L. J.; Luther, G. W.; Lu, Z.; Jonsson, M.; Kloo, L. Angew. Chem., Int. Ed. 2011, 50, 11598.
(g) Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(h) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
(i) Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Chin. J. Org. Chem. 2016, 36, 1973(in Chinese). (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
(g) Zhang, X.; Cong, Y.; Lin, G.; Guo, X.; Cao, Y.; Lei, K.; Du, Y. Chin. J. Org. Chem. 2016, 36, 2513(in Chinese). (张翔, 丛颖, 林光宇, 郭旭亮, 曹阳, 雷坤华, 杜云飞, 有机化学, 2016, 36, 2513.)
(k) Han, Y.; Zhang, C. Tetrahedron Lett. 2018, 59, 3052.
(l) Cai, Q.; Ma, H. Acta Chim. Sinica 2019, 77, 213(in Chinese). (蔡倩, 马浩文, 化学学报, 2019, 77, 213.)
(m) Liu, Dan.; He J.; Zhang, C. Univ. Chem. 2019, 34, 1(in Chinese). (刘丹, 贺家豪, 张弛, 大学化学, 2019, 34, 1.)
[4] Yang, L.; Zhang-Negrerie, D.; Zhao, K.; Du, Y. J. Org. Chem. 2016, 81, 3372.
[5] Yusubov, M. S.; Zhdankin, V. V. Curr. Org. Synth. 2012, 9, 247.
[6] Uyanik M, Ishihara K. ChemCatChem 2012, 4, 177.
[7] Trost, B. M. Science 1991, 254, 1471.
[8] Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259.
[9] (a) Zheng, Z.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Sci. China, Chem. 2014, 57, 189.
(b) Zheng, Z. Ph.D. Dissertation, Tianjing University, Tianji, 2014 (in Chinese). (郑子圣, 博士论文, 天津大学, 天津, 2014.)
(c) Singh, F. V.; Wirth, T. Chem.-Asian J. 2014, 9, 950.
(d) Parra, A.; Reboredo, S. Chem.-Eur. J. 2013, 19, 17244.
[10] Uyanik, M.; Ishihara, K. Chem. Cat. Chem. 2012, 4, 177.
[11] Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
[12] Yamamoto, Y.; Kawano, K.; Toy, P. H.; Togo, H. Tetrahedron 2007, 63, 4680.
[13] Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem., Int. Ed. 2005, 44, 6193.
[14] Dohi, T.; Maruyama, A.; Minamitsuji, Y.; Takenaga, N.; Kita, Y. Chem. Commun. 2007, 1224.
[15] Zhu, C.; Liang, Y.; Hong, X.; Sun, H.; Sun, W.; Houk. K.; Shi, Z. J. Am. Chem. Soc. 2015, 137, 7564
[16] Liang, D.; Yu, W.; Nguyen, N.; Deschamps, J. R.; Imler, G. H.; Li, Y.; MacKerell, A. D.; Jiang, C.; Xue, F. J. Org. Chem. 2017, 82, 3589.
[17] Ito, M.; Kubo, H.; Itani, I.; Morimoto, K.; Dohi, T.; Kita, Y. J. Am. Chem. Soc. 2013, 135, 14078.
[18] Miyamoto, K.; Sakai, Y.; Goda, S.; Ochiai, M. Chem. Commun. 2012, 48, 982.
[19] Philips, B.; Frostick, F. C.; Starcher, P. S. J. Am. Chem. Soc. 1957, 79, 5982.
[20] Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605.
[21] He, Y.; Huang, J.; Liang, D.; Liu, L.; Zhu, Q. Chem. Commun. 2013, 49, 7352.
[22] Wang, X.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2014, 53, 11084.
[23] Shen, C.; Yang, M.; Xu, J.; Chen, C.; Zheng, K.; Shen, J.; Zhang, P. RSC Adv. 2017, 7, 49436.
[24] Braddock, D. C.; Cansell, G.; Hermitage, S. A. Chem. Commun. 2006, 2483.
[25] Fabry, D. C.; Stodulski, M.; Hoerner, S.; Gulder, T. Chem.-Eur. J. 2012, 18, 10834.
[26] Ulmer, A.; Stodulski, M.; Kohlhepp, S. V.; Patzelt, C.; Poethig, A.; Bettray, W.; Gulder, T. Chem.-Eur. J. 2015, 21, 1444.
[27] Patzelt, C.; Alexander, P.; Gulder, T. Org. Lett. 2016, 18, 3466.
[28] Stodulski, M.; Goetzinger, A.; Kohlhepp, S. V.; Gulder, T. Chem. Commun. 2014, 50, 3435.
[29] Liu, H.; Tan, C.-H. Tetrahedron Lett. 2007, 48, 8220.
[30] Alhalib, A.; Kamouka, S.; Moran, W. J. Org. Lett. 2015, 17, 1453.
[31] Morimoto, K.; Sakamoto, K.; Ohshika, T.; Dohi, T.; Kita. Y. Angew. Chem., Int. Ed. 2016, 55, 3652.
[32] Yoshimura, A.; Middleton, K. R.; Luedtke, M. W.; Zhu, C.; Zhdankin, V. V. J. Org. Chem. 2012, 77, 11399.
[33] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
[34] Ma, L.; Wang, X.; Yu, W.; Han, B. Chem. Commun. 2011, 47, 11333.
[35] Zhu, C.; Wei, Y. ChemSusChem 2011, 4, 1082.
[36] Guo, W.; Vallcorba, O.; Vallribera, A.; Shafir, A.; Pleixats, R.; Rius, J. ChemCatChem 2014, 6, 468.
[37] Zhu, C.; Zhang, Y.; Zhao, H.; Huang, S.; Zhang, M.; Su, W. Adv. Synth. Catal. 2015, 357, 331.
[38] Duhamel, T.; Stein, C. J.; Martínez, C.; Reiher, M.; Muñiz. K. ACS Catal. 2018, 8, 3918.
[39] Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933.
[40] Schulze, A.; Giannis, A. Synthesis 2006, 257.
[41] Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251.
[42] Uyanik, M.; Fukatsu, R.; Ishihara, K. Org. Lett. 2009, 11, 3470.
[43] Yusubov, M. S.; Zagulyaeva, A. A.; Zhdankin, V. V. Chem.-Eur. J. 2009, 15, 11091.
[44] Richardson, R. D.; Page, T. K.; Altermann, S.; Paradine, S. M.; French, A. N.; Wirth, T. Synlett 2007, 538.
[45] Fenga, Y.; Huanga, R.; Hua, L.; Xiong, Y.; Coeffard, V. Synthesis 2016, 48, 2637.
[46] Pluta, R.; Krach, P. E.; Cavallo, L.; Falivene, L.; Rueping, M. ACS Catal. 2018, 8, 2582.
[47] Volp, K. A.; Harned, A. M. Chem. Commun. 2013, 49, 3001.
[48] Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 3787.
[49] Dohi, T.; Takenaga, N.; Nakae, T.; Toyoda, Y.; Yamasaki, M.; Shiro, M.; Fujioka, H.; Maruyama, A.; Kita, Y. J. Am. Chem. Soc. 2013, 135, 4558.
[50] Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 2175.
[51] Dohi, T.; Sasa, H.; Miyazaki, K.; Fujitake, M.; Takenaga, N.; Kita, Y. J. Org. Chem. 2017, 82, 11954.
[52] Zhang, D.-Y.; Xu, L.; Wu, H.; Gong, L.-Z. Chem.-Eur. J. 2015, 21, 10314.
[53] Mizar, P.; Laverny, A.; Mohammad. E. S.; Farid, U.; Brown, M.; Malmedy, F.; Wirth, T. Chem. Eur. J. 2014, 20, 9910.
[54] Wu, H.; He, Y.-P.; Xu, L.; Zhang, D.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 3466.
[55] Cao, Y.; Zhang, X.; Lin, G.; Zhang-Negrerie, D.; Du, Y. Org. Lett. 2016, 18, 5580.
[56] Mennie, K. M.; Banik, S. M.; Reichert, E. C.; Jacobsen, E. N. J. Am. Chem. Soc. 2018, 140, 4797.

原位生成的高价碘试剂在有机合成中的应用进展

Recent Advances in the Application of in-situ Generated Hypervalent Iodine Reagents in Organic Synthesis

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