Reviews

Recent Advances of the Application of Organoiodine(Ⅲ) Reagents in the Construction of Heterocyclic Compounds

  • Zhang Xiang ,
  • Cong Ying ,
  • Lin Guangyu ,
  • Guo Xuliang ,
  • Cao Yang ,
  • Lei Kunhua ,
  • Du Yunfei
Expand
  • a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072;
    b Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072

Received date: 2016-05-17

  Revised date: 2016-07-31

  Online published: 2016-08-25

Supported by

Project supported by the National Natural Science Foundation of China (No.21472136),the Tianjin Research Program of Application Foundation and the Ad-vanced Technology (No.15JCZDJC32900) and the National Basic Research Project (No.2015CB856500).

Abstract

Hypervalent iodine chemistry has experienced explosive development over the past 30 years. Being a class of mild, efficient and environmentally benign nonmetal oxidants, hypervalent iodine regents, especially iodine(Ⅲ) oxidants have been widely applied to the construction of various heterocyclic skeletons. In this review, the iodine(Ⅲ)-mediated strategies and methods for the synthesis of heterocyclic compounds with different ring size were highlighted.

Cite this article

Zhang Xiang , Cong Ying , Lin Guangyu , Guo Xuliang , Cao Yang , Lei Kunhua , Du Yunfei . Recent Advances of the Application of Organoiodine(Ⅲ) Reagents in the Construction of Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2016 , 36(11) : 2513 -2529 . DOI: 10.6023/cjoc201605034

References

[1] (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
(b) Moriarty, R. M.; Prakash, O. M. Adv. Heterocycl. Chem. 1997, 69, 1.
(c) Togo, H.; Katohgi, M. Synlett 2001, 565.
(d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
(e) Moreno, I.; Tellitu, I.; Herrero, M. T.; SanMartín, R.; Domínguez, E. Curr. Org. Chem. 2002, 6, 1433.
(f) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
(g) Zhdankin, V. V. Curr. Org. Synth. 2005, 2, 121.
(h) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
(i) Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402.
(j) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
(k) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.
(l) Zhdankin, V. V. ARKIVOC 2009, i, 1.
(m) Duschek, A.; Kirsch, S. F. Angew. Chem., Int. Ed. 2011, 50, 1524.
(n) Brand, J. P.; Gonzalez, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102.
(o). Brown, M.; Farid, U.; Wirth, T. Synlett 2013, 24, 424.
(p) Parra, A.; Reboredo, S. Chem.-Eur. J. 2013, 19, 17244.
(q) Zheng, Z.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Sci. China Chem. 2014, 57, 189.
(r) Narayan, R.; Manna, S.; Antonchick, A. P. Synlett 2015, 26, 1785.
(s) Narayan, R.; Matcha, K.; Antonchick, A. P. Chem.-Eur. J. 2015, 21, 14678.
(t) Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(u) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
(v) Sheng, Q.-J.; Liu, G.-R.; Luo, H.-Q.; Liu, Z.-Q. Chin. J. Org. Chem. 2007, 27, 902 (in Chinese). (盛秋菊, 刘桂荣, 罗海清, 柳忠全, 有机化学, 2007, 27, 902.)
(w) Chen, J.; Qu, H.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937 (in Chinese). (陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
(x) Zhao, Y. D. Chin. J. Org. Chem. 1996, 16, 11 (in Chinese). (赵迎娣, 有机化学, 1996, 16, 11.)
(y) Yang, R. Y.; Dai, L. X. Chin. J. Org. Chem. 1994, 14, 113 (in Chinese). (杨瑞阳, 戴立信, 有机化学, 1994, 14, 113.)
(z) Liang, Y. M.; Chen, B. H.; Wu, X. L.; Ma, Y. X. Chin. J. Synth. Chem. 2002, 10, 98 (in Chinese). (梁永民, 陈保华, 武小莉, 马永祥, 合成化学, 2002, 10, 98.)
[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) Zhdankin, V. V. ARKIVOC 2009, i, 1.
(f) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.
(g) Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094.
(h) Qiu, D.; Zheng, Z.; Mo, F.; Xiao, Q.; Tian, Y.; Zhang, Y.; Wang, J. Org. Lett. 2011, 19, 4988.
(i) Mu, X.; Wu, T.; Wang, H.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878.
(j) Duan, X.; Duan, X.; Yang, K.; Wang, Z.; Zhang, L.; Tong, Y.; Liu, H.; Du, K.; Tang, R. Chin. J. Org. Chem. 2015, 35, 2552.
[3] Kaiho, T. Iodine Chemistry and Applications, John Wiley & Sons, Inc., New York, 2015.
[4] Quideau, S.; Lyvinec, G.; Marguerit, M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.; Chenede, A. Angew. Chem., Int. Ed. 2009, 48, 4605.
[5] (a) Meprathu, B. V.; Protasiewicz, J. D. Tetrahedron 2010, 66, 5768.
(b) Meprathu, B. V.; Protasiewicz, J. D. ARKIVOC 2003, vi, 83.
(c) Song, F.-J.; Wang, C.; Falkowski, J. M.; Ma, L.-Q.; Lin, W.-B. J. Am. Chem. Soc. 2010, 132, 15390.
(d) Song, F.; Wang, C.; Lin, W. Chem. Commun. 2011, 47, 8256.
(e) Kim, S.; Lee, Y. S.; Lee, D. H.; Hyun, M. Y.; Hong, J.-Y.; Huh, S.; Kim, C.; Lee, S. J. Inorg. Chem. Commun. 2013, 31, 29.
[6] Miyamoto, K.; Suzuki, M.; Suefuji, T.; Ochiai, M. Eur. J. Org. Chem. 2013, 2013, 3662.
[7] Li, X. X.; Du, Y. F.; Liang, Z. D.; Li, X. K.; Pan, Y.; Zhao, K. Org. Lett. 2009, 11, 2643.
[8] Sun, X. Q.; Lyu, Y. R.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. Org. Lett. 2013, 15, 6222.
[9] Ton, T. M. U.; Tejo, C.; Tiong, D. L. Y.; Chan, P. W. H. J. Am. Chem. Soc. 2012, 134, 7344.
[10] Kiyokawa, K.; Kosaka, T.; Minakata, S. Org. Lett. 2013, 15, 4858.
[11] Ye, Y.; Zheng, C.; Fan, R. Org. Lett. 2009, 11, 3156.
[12] Ye, Y.; Wang, H.; Fan, R. Org. Lett. 2010, 12, 2802.
[13] Gomes, L. F. R.; Veiros, L. F.; Maulide, N.; Afonso, C. A. M. Chem.-Eur. J. 2015, 21, 1449.
[14] Arisawa, M.; Ramesh, N. G.; Nakajima, M.; Tohma, H.; Kita, Y. J. Org. Chem. 2001, 66, 59.
[15] Ye, Y.; Wang, L.; Fan, R. J. Org. Chem. 2010, 75, 1760.
[16] Dohi, T.; Takenaga, N.; Goto, A.; Maruyama, A.; Kita, Y. Org. Lett. 2007, 9, 3129.
[17] (a) Muraki, T.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1713.
(b) Togo, H.; Muraki, T.; Hoshina, Y.; Yamaguchi, K.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1997, 787.
[18] Liu, H.; Tan, C.-H. Tetrahedron Lett. 2007, 48, 8220.
[19] (a) Karila, D.; Leman, L.; Dodd, R. H. Org. Lett. 2011, 13, 5830.
(b) Geary, G. C.; Hope, E. G.; Stuart, A. M. Angew. Chem., Int. Ed. 2015, 54, 14911.
(c) Boye, A. C.; Meyer, D.; Ingison, C. K.; French, A. N.; Wirth, T. Org. Lett. 2003, 5, 2157.
[20] Karade, N. N.; Shirodkar, S. G.; Patil, M. N.; Potrekar, R. A.; Karade, H. N. Tetrahedron Lett. 2003, 44, 6729.
[21] (a) Cha, J. Y.; Huang, Y.; Pettus, T. R. R. Angew. Chem., Int. Ed. 2009, 48, 9519.
(b) Mendelsohn, B. A.; Lee, S.; Kim, S.; Teyssier, F.; Aulakh, V. S.; Ciufolini, M. A. Org. Lett. 2009, 11, 1539.
(c) Frie, J. L.; Jeffrey, C. S.; Sorensen, E. J. Org. Lett. 2009, 11, 5394.
(d) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
(e) Murakata, M.; Yamada, K.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1994, 443.
(f) Kacan, M.; Koyuncu, D.; McKillop, A. J. Chem. Soc., Perkin Trans. 1 1993, 1771.
(g) Hara, H.; Inoue, T.; Endoh, M.; Nakamura, H.; Takahashi, H.; Hoshino, O. Heterocycles 1996, 42, 4451.
(h) Pierce, J. G.; Kasi, D.; Fushimi, M.; Cuzzupe, A.; Wipf, P. J. Org. Chem. 2008, 73, 7807.
(i) Gu, Y.; Xue, K. Tetrahedron Lett. 2010, 51, 192.
(j) Liu, Q.; Rovis, T. Org. Process Res. Dev. 2007, 11, 598.
[22] Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem., Int. Ed. 2005, 44, 6193.
[23] (a) Uyanik, M.; Yasui, T.; Ishihara, K. Tetrahedron 2010, 66, 5841.
(b) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 2175.
(c) Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Mina-mitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 3787.
[24] Moriarty, R. M.; Prakash, O.; Duncan, M. P.; Vaid, R. K.; Rani, N. J. Chem. Res., Synop. 1996, 9, 432.
[25] Juhasz, L.; Szilagyi, L.; Antus, S.; Visy, J.; Zsila, F.; Simonyi, M. Tetrahedron 2002, 58, 4261.
[26] Kalpogiannaki, D.; Martini, C.-I.; Nikopoulou, A.; Nyxas, J. A.; Pantazi, V.; Hadjiarapoglou, L. P. Tetrahedron 2013, 69, 1566.
[27] (a) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667.
(b) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
(c) Braun, N. A.; Ousmer, M.; Bray, J. D.; Bouchu, D.; Peters, K.; Peters, E.-M.; Ciufolini, M. A. J. Org. Chem. 2000, 65, 4397.
(d) Braun, N. A.; Bray, J. D.; Ciufolini, M. A. Tetrahedron Lett. 1999, 40, 4985.
(e) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7534.
[28] Cui, J.; Jia, Q.; Feng, R.-Z.; Liu, S.-S.; He, T.; Zhang, C. Org. Lett. 2014, 16, 1442.
[29] Francisco, C. G.; Herrera, A. J.; Suarez, E. Tetrahedron:Asymmetry 2000, 11, 3879.
[30] Zhang, P. F.; Chen, Z. C. J. Chem. Res., Synop. 2001, 150.
[31] (a) Kawase, M.; Kitamura, T.; Kikugawa, Y. J. Org. Chem. 1989, 54, 3394.
(b) Kukosha, T.; Trufilkina, N.; Katkevics, M. Synlett 2011, 17, 2525.
(c) Kukosha, T.; Trufilkina, N.; Belyakov, S.; Katkevics, M. Synthesis (Germany) 2012, 44, 2413.
[32] (a) Du, Y. F.; Liu, R. H.; Linn, G.; Zhao, K. Org. Lett. 2006, 8, 5919.
(b) Yu, W. Q.; Du, Y. F.; Zhao, K. Org Lett. 2009, 11, 2417.
(c) Lv, J. L.; Zhang-Negrerie, D.; Deng, J.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 1111.
(d) Shi, H.; Guo, T. J.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. Tetrahedron 2014, 70, 2753.
[33] Sun, J. Y.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2015, 80, 1200.
[34] (a) Boto, A.; Betancor, C.; Hernandez, R.; Rodriguez, M. S.; Suarez, E. Tetrahedron Lett. 1993, 34, 4865.
(b) Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985.
[35] Wang, Y.; Jiang, M.; Liu, J.-T. Chem.-Eur. J. 2014, 20, 15315.
[36] Saito, A.; Matsumoto, A.; Hanzawa, Y. Tetrahedron Lett. 2010, 51, 2247.
[37] Saito, A.; Taniguchi, A.; Kambara, Y.; Hanzawa, Y. Org. Lett. 2013, 15, 2672.
[38] Alhalib, A.; Kamouka, S.; Moran, W. J. Org. Lett. 2015, 17, 1453.
[39] (a) Yoshimura, A.; Middleton, K. R.; Todora, A. D.; Kastern, B. J.; Koski, S. R.; Maskaev, A. V.; Zhdankin, V. V. Org. Lett. 2013, 15, 4010.
(b) Xiang, C.; Li, T.; Yan, J. Synth. Commun. 2014, 44, 682.
[40] Han, L.; Zhang, B.; Xiang, C.; Yan, J. Synthesis 2014, 46, 503.
[41] Yu, Z.; Ma, L.; Yu, W. Synlett 2012, 23, 1534.
[42] Zhao, F.; Liu, X.; Qi, R.; Zhang-Negrerie, D.; Huang, J. H.; Du, Y. F.; Zhao, K. J. Org. Chem. 2011, 76, 10338.
[43] (a) Ueno, M.; Nabana, T.; Togo, H. J. Org. Chem. 2003, 68, 6424.
(b) Moriarty, R. M.; Vaid, R. K.; Duncan, M. P. Tetrahedron Lett. 1988, 29, 6913.
[44] (a) Das, B.; Srinivas, Y.; Holla, H.; Krishnaiah, M.; Narender, R. Chem. Lett. 2007, 1270.
(b) Du, L. H.; Wang, Y. G. Synthesis 2007, 675.
[45] (a) Kumar, A.; Maurya, R. A.; Ahmad, P. J. Comb. Chem. 2009, 11, 198.
(b) Saito, A.; Kambara, Y.; Yagyu, T.; Noguchi, K.; Yoshimura, A.; Zhdankin, V. V. Adv. Synth. Catal. 2015, 357, 667.
[46] He, T.; Gao, W. C.; Wang, W. K.; Zhang, C. Adv. Synth. Catal. 2014, 356, 1113.
[47] Prakash, O.; Batra, H.; Kaur, H.; Sharma, P. K.; Sharma, V.; Singh, S. P.; Moriarty, R. M. Synthesis 2001, 541.
[48] Kotali, A. J. Heterocycl. Chem. 1996, 33, 605.
[49] Zheng, Z. S.; Ma, S. Y.; Tang, L. L.; Zhang-Negrerie, D.; Deng, J.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 4687.
[50] Kita, Y.; Egi, M.; Ohtsubo, M.; Saiki, T.; Takada, T.; Tohma, H. Chem. Commun. 1996, 2225.
[51] Downer-Riley, N. K.; Jackson, Y. A. Tetrahedron 2008, 64, 7741.
[52] Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. Org. Lett. 2006, 8, 4811.
[53] (a) Moriarty, R. M.; Tyagi, S. Org. Lett. 2010, 12, 364.
(b) Katohgi, M.; Togo, H.; Yamaguchi, K.; Yokoyama, M. Tetrahedron 1999, 55, 14885.
[54] Inagaki, T.; Nakamura, Y.; Sawaguchi, M.; Yoneda, N.; Ayuba, S.; Hara, S. Tetrahedron Lett. 2003, 44, 4117.
[55] Fujioka, H.; Komatsu, H.; Nakamura, T.; Miyoshi, A.; Hata, K.; Ganesh, J.; Murai, K.; Kita, Y. Chem. Commun. 2010, 46, 4133.
[56] Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.; Sugimura, T. Angew. Chem., Int. Ed. 2010, 49, 7068.
[57] Wang, X.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2014, 53, 11084.
[58] (a) Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 4, 581.
(b). Romero, A. G. Darlington, W. H.; Jacobsen, E. J.; Mickelson, J. W. Tetrahedron Lett. 1996, 37, 2361.
(c) Tellitu, I.; Urrejola, A.; Serna, S.; Moreno, I.; Herrero, M. T.; Dominguez, E.; SanMartin, R.; Correa, A. Eur. J. Org. Chem. 2007, 437.
(d) Herrero, M. T.; Tellitu, I.; Dominguez, E.; Hernandez, S.; Moreno, I.; SanMartin, R. Tetrahedron 2002, 58, 8581.
(e) Herrero, M. T.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Tetrahedron Lett. 2002, 43, 8273.
(f) Correa, A.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. J. Org. Chem. 2005, 70, 2256.
(g) Churruca, F.; SanMartin, R.; Tellitu, I.; Dominguez, E. Eur. J. Org. Chem. 2005, 2481.
(h) Serna, S.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Tetrahedron 2004, 60, 6533.
(i) Churruca, F.; SanMartin, R.; Carril, M.; Urtiaga, M. K.; Solans, X.; Tellitu, I.; Dominguez, E. J. Org. Chem. 2005, 70, 3178.
(j) Herrero, M. T.; Tellitu, I.; Hernandez, S.; Dominguez, E.; Moreno, I.; SanMartin, R. ARKIVOC 2002, v, 31.
(k) Serna, S.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Tetrahedron Lett. 2003, 44, 3483.
(l) Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. J. Org. Chem. 2006, 71, 8316.
(m) Serna, S.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Org. Lett. 2005, 7, 3073.
(n) Tellitu, I.; Serna, S.; Herrero, M. T.; Moreno, I.; Dominguez, E.; SanMartin, R. J. Org. Chem. 2007, 72, 1526.
(o) Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. J. Org. Chem. 2006, 71, 3501.
(p) Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. Tetrahedron 2006, 62, 11100.
(q) Zhang, X.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2013, 78, 12750.
[59] Kita, Y.; Watanabe, H.; Egi, M.; Saiki, T.; Fukuoka, Y.; Tohma, H. J. Chem. Soc., Perkin Trans. 1 1998, 635.
[60] Koag, M.; Lee, S. Org. Lett. 2011, 13, 4766.
[61] (a) Kong, W.; Feige, P.; de Haro, T.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 2469.
(b) Suzuki, S.; Kamo, T.; Fukushi, K.; Hiramatsu, T.; Tokunaga, E.; Dohi, T.; Kita, Y.; Shibata, N. Chem. Sci. 2014, 5, 2754.
(c) Yuan, W.; Szabo, K. Angew. Chem., Int. Ed. 2015, 54, 8533.
[62] Okamoto, N.; Miwa, Y.; Minami, H.; Takeda, K.; Yanada, R. Angew. Chem., Int. Ed. 2009, 48, 9693.
[63] Yang, C.; Zhang, X.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2015, 80, 5320.
[64] (a) Chen, Z.-W.; Zhu, Y.-Z.; Ou, J.-W.; Wang, Y.-P.; Zheng, J.-Y. J. Org. Chem. 2014, 79, 10988.
(b) Manna, S.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 7324.
[65] Liu, L.; Lu, H.; Wang, H.; Yang, C.; Zhang, X.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. Org. Lett. 2013, 15, 2906.
[66] (a) Taylor, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 11377.
(b) Tohma, H.; Morioka, H.; Takizawa, S.; Arisawa, M.; Kita, Y. Tetrahedron 2001, 57, 345.
(c) Moreno, I.; Tellitu, I.; Etayo, J.; SanMartin, R.; Dominguez, E. Tetrahedron 2001, 57, 5403.
[67] Ishiwata, Y.; Togo, H. Tetrahedron Lett. 2009, 50, 5354.
[68] Liu, H.; Wei, Y. Tetrahedron Lett. 2013, 54, 4645.
[69] (a) Zhang, N.; Cheng, R.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem. 2014, 79, 10581.
(b) Yang, L.; Zhang-Negrerie, D.; Zhao, K.; Du, Y. F. J. Org. Chem. 2016, 81, 3372.
[70] Takada, T.; Arisawa, M.; Gyoten, M.; Hamada, R.; Tohma, H.; Kita, Y., J. Org. Chem. 1998, 63, 7698.
[71] (a) Li, X. M.; Yang, L.; Zhang, X.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 955.
(b) Guo, X. L.; Zhang-Negrerie, D.; Du, Y. F. RSC Adv. 2015, 5, 94732.
[72] Shang, S. Y.; Zhang-Negrerie, D.; Du, Y. F.; Zhao, K. Angew. Chem., Int Ed. 2014, 53, 6216.
[73] Kitamura, T.; Yamane, M.; Inoue, K.; Todaka, M.; Fukatsu, N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674.
[74] Ngatimin, M.; Frey, R.; Levens, A.; Nakano, Y.; Kowalczyk, M.; Konstas, K.; Hutt, O. E.; Lupton, D. W. Org. Lett. 2013, 15, 5858.
[75] Chanu, A.; Safir, I.; Basak, R.; Chiaroni, A.; Arseniyadis, S. Eur. J. Org. Chem. 2007, 26, 4305.
[76] Cook, S. P.; Danishefsky, S. J. Org. Lett. 2006, 8, 5693.
[77] (a) Muniz, K. J. Am. Chem. Soc. 2007, 129, 14542.
(b) Kim, H. J.; Cho, S. H.; Chang, S. Org. Lett. 2012, 14, 1424.
[78] (a) Huang, X. H.; Shao, N.; Palani, A.; Aslanian, R.; Buevich, A.; Seidel-Dugan, C.; Huryk, R. Tetrahedron Lett. 2008, 49, 3592.
[79] Mizar, P.; Laverny, A.; El-Sherbini, M.; Farid, U.; Brown, M.; Malmedy, F.; Wirth, T. Chem.-Eur. J. 2014, 20, 9910.
[80] Wang, J. W.; Yuan, Y. C.; Xiong, R.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Org Lett. 2012, 14, 2210.
[81] Wu, H.; He, Y.-P.; Xu, L.; Zhang, D.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 3466.
[82] Zhang, X.; Yang, C.; Zhang-Negrerie, D.; Du, Y. Chem.-Eur. J. 2015, 21, 5193.
[83] Zhang, X.; Hou, W. J.; Zhang-Negrerie, D.; Zhao, K.; Du, Y. F. Org. Lett. 2015, 17, 5252.
[84] Zhang, D.-Y.; Xu, L.; Wu, H.; Gong, L.-Z. Chem.-Eur. J. 2015, 21, 10314.

Outlines

/

〈 〉