Citation: Cai Qian, Ma Haowen. Recent Advances of Chiral Hypervalent Iodine Reagents[J]. Acta Chimica Sinica, ;2019, 77(3): 213-230. doi: 10.6023/A18110470 shu

Recent Advances of Chiral Hypervalent Iodine Reagents

Cai Qian ^, ,
Ma Haowen

College of Pharmacy, Jinan University, Guangzhou 510530

Corresponding author: Cai Qian, caiqian@jnu.edu.cn
Received Date: 21 November 2018
Available Online: 28 March 2019
Fund Project: the National Natural Science Foundation of China 21772066Guangdong Special Support Program 2017TX04R059Project supported by the National Natural Science Foundation of China (Nos. 21772066, 21572229) and Guangdong Special Support Program (No. 2017TX04R059)the National Natural Science Foundation of China 21572229

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Hypervalent iodine chemistry has arose as an important field in organic chemistry in the past decades. Hypervalent iodine compounds, with reactivities similarly to transition metals in many different types of transformations, have attracted broad interests in organic community due to their practical advantages in the mild conditions, low costs, environmental benign and low toxicity. Great progresses have been made in this field. Chiral hypervalent iodine reagents or precursors have also been developed and utilized in a variety of asymmetric reactions in a stoichiometric or catalytic way. Important advances have been witnessed in the field of chiral hypervalent iodine chemistry in recent years. However, great limitations still exist. In this review, we have made a summary of different types of chiral hypervalent iodine reagents and precursors according to the characteristics of these compounds and the timeline. It may be helpful for the researchers to better understand the development and limitations of chiral hypervalent iodine chemistry.
- chirality,
- chiral hypervalent iodine,
- chiral aryl iodide,
- asymmetric reaction,
- catalytic asymmetric synthesis
1. [1]
  For books, see: (a) Chemistry of Hypervalent Compounds, Ed.: AKiba, K. Y., Wiley-VCH, New York, 1999. (b) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure and Syn-thetic Application of Polyvalent Iodine Compounds, John Wiley & Sons Ltd., New York, 2014. (c) Iodine Chemistry And Applications, Ed.: Kaiho, T., John Wiley & Sons Ltd., New York, 2015. (d) Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, Ed.: Wirth, T., Springer, 2003.
2. [2]
  For recent reviews, see: (a) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. (b) 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. ) (c) Ma, J.; Chen, L.; Yuan, Z.; Cheng, H. Chin. j. Org. Chem. 2018, 38, 1586(in Chinese). (马姣丽, 陈立成, 袁中文, 程辉成, 有机化学, 2018, 38, 1586. )
3. [3]
  For selected recent reviews, see: (a) Flores, A.; Cots, E.; Bergès, J.; Muñiz, K. Adv. Synth. Catal. 2019, 361, DOI: 10.1002/adsc. 201800521. (b)MartínRomero,R.; Wöste,T. H.; Muñiz,K. Chem. AsianJ. 2014,9,972. (c)Singh,F. V.; Wirth,T. Chem. AsianJ. 2014,9,950. (d)Harned,A. M. TetrahedronLett. 2014,55,4681. (e)Parra,A.; Reboredo, S. Chem. Eur. J. 2013,19,17244.
4. [4]
  Liang, H.; Ciufolini, M. A. Angew. Chem. Int. Ed. 2011, 50, 11849. doi: 10.1002/anie.v50.50
5. [5]
  Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. j. Am. Chem. Soc. 2005, 127, 12244. (b) Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193.
6. [6]
  Pribram, R. Justus Liebigs Ann. Chem. 1907, 351, 481. doi: 10.1002/(ISSN)1099-0690
7. [7]
  Imamoto, T.; Koto, H. Chem. Lett. 1986, 967.
8. [8]
  Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. j. Org. Chem. 1990, 55, 315. doi: 10.1021/jo00288a053
9. [9]
  Xia, M.; Chen, Z.-C. Synth. Commun. 1997, 27, 1321. doi: 10.1080/00397919708006060
10. [10]
  Ray Ⅲ, D. G.; Koser, G. F. j. Am. Chem. Soc. 1990, 112, 5672. doi: 10.1021/ja00170a059
11. [11]
  Ray Ⅲ D. G.; Koser, G. F. j. Org. Chem. 1992, 57, 1607. doi: 10.1021/jo00031a054
12. [12]
  Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.; Maegawa, T.; Kita, Y. j. Org. Chem. 1999, 64, 3519. doi: 10.1021/jo982295t
13. [13]
  Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453. doi: 10.1016/0040-4039(96)01436-0
14. [14]
  (a) Wirth, T.; Hirt, U. H. Tetrahedron Asymmetry 1997, 8, 23. (b) Hirt, U. H.; Spingler, B.; Wirth, T. j. Org. Chem. 1998, 63, 7674. (c) Hirt, U. H.; Schuster, M. F. H.; French, A. N.; Wiest, O. G.; Wirth, T. Eur. j. Org. Chem. 2001, 1569.
15. [15]
  Mizar, P.; Laverny, A.; EI-Sherbini, M.; Farid, U.; Brown, M.; Malmedy, F.; Wirth, T. Chem. Eur. j. 2014, 20, 9910. doi: 10.1002/chem.201403891
16. [16]
  Hempel, C.; Maichle-Mössmer, C.; Pericàs, M. A.; Nachtsheim, B. j. Adv. Synth. Catal. 2017, 359, 2941.
17. [17]
  Fujita, M.; Okuno, S.; Lee, H. J.; Sugimura, T.; Okuyama, T. Tetrahedron Lett. 2007, 48, 8691. doi: 10.1016/j.tetlet.2007.10.015
18. [18]
  (a) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem. Int. Ed. 2010, 49, 2175. (b) Uyanik, M.; Yasui, T.; Ishihara, K. Tetrahedron 2010, 66, 5841.
19. [19]
  (a) Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.; Sugimura, T. Angew. Chem. Int. Ed. 2010, 49, 7068. (b) Fujita, M.; Mori, K.; Shimogaki, M.; Sugimura, T. Org. Lett. 2012, 14, 1294. (c) Shimogaki, M.; Fujita, M.; Sugimura, T. Eur. j. Org. Chem. 2013, 7128. (d) Takesue, T.; Fujita, M.; Sugimura, T.; Akutsu, H. Org. Lett. 2014, 16, 4634.
20. [20]
  Fujita, M.; Wakita, M.; Sugimura, T. Chem. Commun. 2011, 47, 3983. doi: 10.1039/c1cc10129c
21. [21]
  (a) Shimogaki, M.; Fujita, M.; Sugimura, T. Angew. Chem. Int. Ed. 2016, 55, 15797. (b) Shimogaki, M.; Fujita, M.; Sugimura, T. j. Org. Chem. 2017, 82, 11836.
22. [22]
  Röben, C.; Souto, j. A.; González, Y.; Lishchynskyi, A.; Muñiz, K. Angew. Chem. Int. Ed. 2011, 50, 9478. doi: 10.1002/anie.v50.40
23. [23]
  Muñiz, K.; Barreiro, L.; Romero, R. M.; Martínez, C. j. Am. Chem. Soc. 2017, 139, 4354. doi: 10.1021/jacs.7b01443
24. [24]
  (a) Haubenreisser, S.; Wöste, T. H.; Martínez, C.; Ishihara, K.; Muñiz, K. Angew. Chem. Int. Ed. 2016, 55, 413. (b) Wöste, T. H.; Muñiz, K. Synthesis 2016, 48, 816.
25. [25]
  (a) Farid, U.; Wirth, T. Angew. Chem. Int. Ed. 2012, 51, 3462. (b) Mizar, P.; Niebuhr, R.; Hutchings, M.; Farooq, U.; Wirth, T. Chem. Eur. J. 2016, 22, 1614.
26. [26]
  Gelis, C.; Dumoulin, A.; Bekkaye, M.; Neuville, L.; Masson, G. Org. Lett. 2017, 19, 278. doi: 10.1021/acs.orglett.6b03631
27. [27]
  (a) Kong, W.; Feige, P.; de Haro, T.; Nevado, C. Angew. Chem. Int. Ed. 2013, 52, 2469. (b) Pluta, R.; Krach, P. E.; Cavallo, L.; Falivene, L.; Rueping, M. ACS Catal. 2018, 8, 2582.
28. [28]
  Wu, H.; He, Y.-P.; Xu, L.; Zhang, D.-Y.; Gong, L.-Z. Angew. Chem. Int. Ed. 2014, 53, 3466. doi: 10.1002/anie.201309967
29. [29]
  Zhang, D.-Y.; Xu, L.; Wu, H.; Gong, L.-Z. Chem. Eur. j. 2015, 21, 10314. doi: 10.1002/chem.201501583
30. [30]
  Cao, Y.; Zhang, X.; Lin, G.; Zhang-Negrerie, D.; Du, Y. Org. Lett. 2016, 18, 5580. doi: 10.1021/acs.orglett.6b02816
31. [31]
  Farid, U.; Malmedy, F.; Claveau, R.; Albers, C.; Wirth, T. Angew. Chem. Int. Ed. 2013, 52, 7018. doi: 10.1002/anie.201302358
32. [32]
  Brown, M.; Kumar, R.; Rehbein, J.; Wirth, T. Chem. Eur. j. 2016, 22, 4030. doi: 10.1002/chem.201504844
33. [33]
  Banik, S. M.; Medley, j. W.; Jacobsen, E. N. j. Am. Chem. Soc. 2016, 138, 5000. doi: 10.1021/jacs.6b02391
34. [34]
  Banik, S. M.; Medley, j. W.; Jacobsen, E. N. Science 2016, 353, 51. doi: 10.1126/science.aaf8078
35. [35]
  Zhou, B.; Haj, M. K.; Jacobsen, E. N.; Houk, K. N.; Xue, X.-S. j. Am. Chem. Soc. 2018, 140, 15206. doi: 10.1021/jacs.8b05935
36. [36]
  Mennie, K. M.; Banik, S. M.; Reichert, E. C.; Jacobsen, E. N. j. Am. Chem. Soc. 2018, 140, 4797. doi: 10.1021/jacs.8b02143
37. [37]
  Qurban, J.; Elsherbini, M.; Wirth, T. j. Org. Chem. 2017, 82, 11872. doi: 10.1021/acs.joc.7b01571
38. [38]
  Hashimoto, T.; Shimazaki, Y.; Omatsu, Y.; Maruoka, K. Angew. Chem. Int. Ed. 2018, 57, 7200. doi: 10.1002/anie.v57.24
39. [39]
  Zhdandin, V. V.; Smart, j. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299. doi: 10.1016/S0040-4039(00)00836-4
40. [40]
  Ladziata, U.; Carlson, J.; Zhdankin, V. V. Tetrahedron Lett. 2006, 47, 6301. doi: 10.1016/j.tetlet.2006.06.103
41. [41]
  Altermann, S. M.; Richardson, R. D.; Page, T. K.; Schmidt, R. K.; Holland, E.; Mohammed, U.; Paradine, S. M.; French, A. N.; Richter, C.; Bahar, A. M.; Witulski, B.; Wirth, T. Eur. j. Org. Chem. 2008, 5315.
42. [42]
  Farooq, U.; Schäfer, S.; Ali Shah, A.-U.-H.; Freudendahl, D. M.; Wirth, T. Synthesis 2010, 1023.
43. [43]
  Volp, K. A.; Harned, A. M. Chem. Commun. 2013, 49, 3001. doi: 10.1039/c3cc00013c
44. [44]
  Boppisetti, j. K.; Birman, V. B. Org. Lett. 2009, 6, 1221.
45. [45]
  Guilbault, A.-A.; Basdevant, B.; Wanie, V.; Legault, C. Y. j. Org. Chem. 2012, 77, 11283. doi: 10.1021/jo302393u
46. [46]
  Rodríguez, A.; Moran, W. j. Synthesis 2012, 44, 1178. doi: 10.1055/s-0031-1290590
47. [47]
  Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem. Int. Ed. 2013, 52, 9215. doi: 10.1002/anie.201303559
48. [48]
  Uyanik, M.; Sasakura, N.; Mizuno, M.; Ishihara, K. ACS Catal. 2017, 7, 872. doi: 10.1021/acscatal.6b03380
49. [49]
  Uyanik, M.; Yasui, Y.; Ishihara, K. j. Org. Chem. 2017, 82, 11946. doi: 10.1021/acs.joc.7b01941
50. [50]
  Jain, N.; Xu, S.; Ciufolini, M. A. Chem. Eur. j. 2017, 23, 4542. doi: 10.1002/chem.201700667
51. [51]
  Molnár, I. G.; Gilmour, R. j. Am. Chem. Soc. 2016, 138, 5004. doi: 10.1021/jacs.6b01183
52. [52]
  Scheidt, F.; Schäfer, M.; Sarie, j. C.; Doniliuc, C. G.; Molloy, j. J.; Gilmour, R. Angew. Chem. Int. Ed. 2018, 57, 16431. doi: 10.1002/anie.201810328
53. [53]
  Ochiai, M.; Takaoka, Y.; Masaki, Y. j. Am. Chem. Soc. 1990, 112, 5677. doi: 10.1021/ja00170a063
54. [54]
  Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. j. Am. Chem. Soc. 1999, 121, 9234.
55. [55]
  Deng, Q.-H.; Wang, j.-C.; Xu, Z.-J.; Zhou, C.-Y.; Che, C.-M. Synthesis 2011, 18, 2959.
56. [56]
  Quideau, S.; Lyvinec, G.; Marguerit, M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.; Chénedé, A. Angew. Chem. Int. Ed. 2009, 48, 4605. doi: 10.1002/anie.v48:25
57. [57]
  Bosset, C.; Coffinier, R.; Peixoto, P. A.; Assal, M. E.; Miqueu, K. M.; Sotiropoulos, j.-M. Pouységu, L.; Quideau, S. Angew. Chem. Int. Ed. 2014, 53, 9860. doi: 10.1002/anie.201403571
58. [58]
  Companys, S.; Peixoto, P. A.; Bosset, C.; Chassaing, S.; Miqueu, K.; Sotiropoulos, j.-M.; Pouységu, L.; Quideau, S. Chem. Eur. j. 2017, 23, 13309. doi: 10.1002/chem.v23.54
59. [59]
  (a) Brenet, S.; Berthiol, F.; Einhorn, j. Eur. j. Org. Chem. 2013, 8094. (b) Brenet S.; Minozzi, C.; Clarens, B.; Amiri, L.; Berthiol, F. Synthesis 2015, 47, 3859
60. [60]
  Dohi, T.; Sasa, H.; Miyazaki, K.; Fujitake, M.; Takenaga, N.; Kita, Y. j. Org. Chem. 2017, 82, 11954. doi: 10.1021/acs.joc.7b02037
61. [61]
  Levitre, G.; Dumoulin, A.; Retailleau, P.; Panossian, A.; Leroux, F. R.; Masson, G. j. Org. Chem. 2017, 82, 11877. doi: 10.1021/acs.joc.7b01597
62. [62]
  Xue, j.-H.; Zhou, Q.-L. Acta Chim. Sinica 2014, 72, 778(in Chinese).
63. [63]
  Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem. Int. Ed. 2008, 47, 3787. doi: 10.1002/(ISSN)1521-3773
64. [64]
  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. doi: 10.1021/ja401074u
65. [65]
  Yu, J.; Cui, J.; Hou, X.-S.; Liu, S.-S.; Gao, W.-C.; Jiang, S.; Tian, J.; Zhang, C. Tetrahedron: Asymmetry 2011, 22, 2039. doi: 10.1016/j.tetasy.2011.12.003
66. [66]
  Ding, Q.; He, H.; Cai, Q. Org. Lett. 2018, 20, 4554. doi: 10.1021/acs.orglett.8b01849
67. [67]
  Wang, Y.; Yuan, H.; Lu, H.; Zheng, W.-H. Org. Lett. 2018, 20, 2555. doi: 10.1021/acs.orglett.8b00711
68. [68]
  Murray, S. J.; Müller-Bunz, H.; Ibrahim, H. Chem. Commun. 2012, 48, 6268. doi: 10.1039/c2cc32280c
69. [69]
  Ogasawara, M.; Sasa, H.; Hu, H.; Amano, Y.; Nakajima, H.; Takenaga, N.; Nakajima, K.; Kita, Y.; Takahashi, T.; Dohi, T. Org. Lett. 2017, 19, 4102. doi: 10.1021/acs.orglett.7b01876
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