Citation: Ma Jiaoli, Chen Licheng, Yuan Zhongwen, Cheng Huicheng. Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1586-1595. doi: 10.6023/cjoc201802021 shu

Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom

College of Chemcal Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Corresponding author: Cheng Huicheng, awchengcheng@163.com
Received Date: 22 February 2018
Revised Date: 2 April 2018
Available Online: 13 July 2018
Fund Project: Project supported by the Maoming City Technology Bureau (No. 917313), the Guangdong University of Petrochemical Technology (Nos. 517152, 517136, 2017pyA006)

Figures(9)

As a kind of low toxicity, environmentally friendly, high reaction activity reagent, hypervalent iodine compounds have received the widespread attention. Acyclic diaryl iodonium salt as aryl cationic reagent, has an important application in organic synthesis. Under mild conditions, diaryl iodonium salt can react with nucleophilic reagent, which has been one of the effective means of the arylation of heteroatom. According to the classification of chemical bond formation, the application of the acyclic diaryl iodonium salt in the arylation of heteroatom (including oxygen, nitrogen, sulfur, phosphorus, etc.) is discussed and the development direction in the field is prospected.
- acyclic diaryl iodonium salt,
- heteroatom,
- arylation
1. [1]
  (a) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds, Wiley, Chichester, 2013.
  (b) Wirth, T. Hypervalent Iodine Chemistry, Springer, Berlin, 2003.
  (c) Varvoglis, A. Hypervalent Iodine in Organic Syntheses, Academic Press, San Diego, 1996.
  (d) Zhdankin, V. V. ARKIVOC 2009, (i), 1.
  (e) Wirth, T. Angew. Chem. Int. Ed. 2005, 117, 3722.
  (f) Richardson, R. D. ; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402.
  (g) Zhang, X. ; Cong, Y. ; Lin, G. -Y. ; Guo, X. -L. ; Cao, Y. ; Lei, K. -H. ; Du, Y. -F. 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.)
  (h) Duan, Y. -N. ; Jiang, S. ; Han, Y. -C. ; Sun, B. ; Zhang, C. J. Org. Chem. 2016, 36, 973 (in Chinese).
  (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
2. [2]
  (a) Koser, G. F. ; Wettach, R. H. ; Smith, C. S. J. Org. Chem. 1980, 45, 1543.
  (b) Stang, P. J. ; Zhdankin, V. V. ; Tykwinski, R. Tetrahedron Lett. 1992, 33, 1419.
  (c) Merritt, E. A. ; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052.
  (d) Bielawski, M. ; Olofsson, B. Chem. Commun. 2007, 25, 2521.
  (e) Bielawski, M. ; Zhu, M. ; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610.
  (f) Bielawski, M. ; Olofsson, B. Chem. Commun. 2007, 2521.
  (g) Zhu, M. ; Jalalian, N. ; Olofsson, B. Synlett 2008, 592.
  (h) Yusubov, M. S. ; Maskaev, A. V. ; Zhdankin, V. V. ARKIVOC 2011, (i), 370.
  (i) Xiao, Z. -C. ; Xia, C. -F. Chin. J. Org. Chem. 2013, 33, 2119 (in Chinese).
  (肖志超, 夏成峰, 有机化学, 2013, 33, 2119.)
  (j) Zhang, B. -X. ; Zhao, X. -Y. ; Wu, Q. ; Guo, Y. -L. Prog. Chem. 2013, 25, 1142 (in Chinese).
  (张变香, 赵晓芸, 吴群, 郭一力, 化学进展, 2013, 25, 1142.)
  (k) Olofsson, B. Top. Curr. Chem. 2015, 373, 135. (l) Aradi, K. ; Tóth, B. L. ; Tolnai, G. L. ; Novák, Z. Synlett 2016, 27, 1456.
3. [3]
  Hartmann, C.; Meyer, V. Ber. Dtsch. Chem. Ges. 1894, 27, 426. doi: 10.1002/(ISSN)1099-0682
4. [4]
  (a) Koser, G. F. ; Wettach, R. H. ; Smith, C. S. J. Org. Chem. 1980, 45, 1543.
  (b) Carman C. S. ; Koser G. F. J. Org. Chem. 1983, 48, 2534.
  (c) Margida A. J. ; Koser G. F. J. Org. Chem. 1984, 49, 3643.
  (d) Kitamura T. ; Matsuyuki J. ; Taniguchi H. Synthesis 1994, 147.
  (e) Mascarelli, L. ; Benati. G. Gazz. Chim Ital. 1908, 38, 627.
  (f) Merritt, E. A. ; Malmgren, J. ; Klinke, F. J. ; Olofsson, B. Synlett 2009, 2277.
  (g) Bielawski, M. ; Aili, D. ; Olofsson, B. J. Org. Chem. 2008, 73, 4602.
  (h) Lindstedt, E. ; Reitti, M. ; Olofsson, B. J. Org. Chem. 2017, 82, 11909.
  (i) Grushin, V. V. Chem. Soc. Rev. 2000, 29, 315.
  (j) Chatterjee, N. ; Goswami, A. Eur. J. Org. Chem. 2017, 3023.
5. [5]
  (a) Stang P. J. ; Zhdankin V. V. Chem. Rev. 1996, 96, 1123.
  (b) Olofsson B. ; Merritt. E. A. Angew. Chem., Int. Ed. 2009, 48, 9052.
6. [6]
  (a) Der Puy, M. V. J. Fluorine Chem. 1982, 21, 385.
  (b) Pike, V. W. ; Aigbirhio, F. I. J. Chem. Soc., Chem. Commun. 1995, 2215.
  (c)Shah, A. ; W. Pike, V. ; A. Widdowson, D. J. Chem. Soc., Perkin Trans. 1 1998, (13), 2043.
  (d) Graskemper, J. W. ; Wang, B. ; Qin, L. ; Neumann, K. D. ; DiMagno, S. G. Org. Lett. 2011, 13, 3158.
7. [7]
  (a) Ichiishi, N. ; Canty, A. J. ; Yates, B. F. ; Sanford, M. S. Org. Lett. 2013, 15, 5134.
  (b)Ichiishi, N. ; Canty, A. J. ; Yates, B. F. ; Sanford, M. S. Organometallics 2014, 33, 5525.
  (c) Ichiishi, N. ; Brooks, A. F. ; Topczewski, J. J. ; Rodnick, M. E. ; Sanford, M. S. ; Scott, P. J. H. Org. Lett. 2014, 16, 3224.
8. [8]
  Moon, B. S.; Kil, H. S.; Park, J. H.; Kim, J. S.; Park, J.; Chi, D. Y.; Lee, B. C.; Kim, S. E. Org. Biomol. Chem. 2011, 9, 8346. doi: 10.1039/c1ob06277h
9. [9]
  Chun, J.-H.; Pike, V. W. Org. Biomol. Chem. 2013, 11, 6300. doi: 10.1039/c3ob41353e
10. [10]
  (a) Rotstein, B. H. ; Stephenson, N. A. ; Vasdev, N. ; Liang, S. H. Nat. Commun. 2014, 5, 4365.
  (b) Calderwood, S. ; Collier, T. L. ; Gouverneur, V. ; Liang, S. H. ; Vasdev, N. J. Fluorine Chem. 2015, 178, 249.
11. [11]
  Carrol, M. A.; Wood, R. A. Tetrahedron 2007, 63, 11349. doi: 10.1016/j.tet.2007.08.076
12. [12]
  Sandtorv, A. H.; Stuart, D. R. Angew. Chem., Int. Ed. 2016, 55, 15812. doi: 10.1002/anie.201610086
13. [13]
  Yang, Y.; Wu, X.; Han, J.; Mao, S.; Qian, X.; Wang, L. Eur. J. Org. Chem. 2014, 6854.
14. [14]
  Riedmüller, S.; Nachtsheim, B. J. Synlett 2015, 26, 651. doi: 10.1055/s-00000083
15. [15]
  Pang, X.; Lou, Z.; Li, M.; Wen, L.; Chen, C. Eur. J. Org. Chem. 2015, 3361.
16. [16]
  Geng, X.; Mao, S.; Chen, L.; Yu, J.; Han, J.; Hua, J.; Wang, L. Tetrahedron Lett. 2014, 55, 3856. doi: 10.1016/j.tetlet.2014.05.082
17. [17]
  Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.; Olofsson, B. Org. Lett. 2015, 17, 2688. doi: 10.1021/acs.orglett.5b01079
18. [18]
  Lucchetti, N.; Scalone, M.; Fantasia, S.; Muiz, K. Angew. Chem., Int. Ed. 2016, 55, 13335. doi: 10.1002/anie.201606599
19. [19]
  Yang, Q.; He, X.-X.; Chang, J.; Wu, Q.; Zhang, B.-X. Chin. J. Org. Chem. 2011, 31, 1687 (in Chinese).
20. [20]
  Guo, F.; Wang, L.; Wang, P.; Yu, J.; Han, J. Asian J. Org. Chem. 2012, 1, 218. doi: 10.1002/ajoc.v1.3
21. [21]
  Gonda, Zs.; Novák, Z. Chem. Eur. J. 2015, 21, 16801. doi: 10.1002/chem.v21.47
22. [22]
  Modha, S. G.; Greaney, M. F. J. Am. Chem. Soc. 2015, 137, 1416. doi: 10.1021/ja5124754
23. [23]
  Reitti, M.; Villo, P.; Olofsson, B. Angew. Chem. Int. Ed. 2016, 55, 8928. doi: 10.1002/anie.201603175
24. [24]
  Li, X.; Li, L.; Mo, X.; Mo, D. Synth. Commun. 2016, 46, 963. doi: 10.1080/00397911.2016.1181764
25. [25]
  Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323. doi: 10.1002/anie.201300586
26. [26]
  Su, X.; Chen, C.; Wang, Y.; Chen, J.; Lou, Z.; Li, M. Chem. Commun. 2013, 49, 6752. doi: 10.1039/c3cc43216e
27. [27]
  (a) Cahard, E. ; Bremeyer, N. ; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 9284.
  (b) Sinai, Á. ; Mészáros, Á. ; Gáti, T. ; Kudar, V. ; Pallò, A. ; Novák, Z. Org. Lett. 2013, 15, 5654.
  (c) Wang, Y. ; Chen, C. ; Peng, J. ; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323.
  (d) Zhang, F. ; Das, S. ; Walkinshaw, A. J. ; Casitas, A. ; Taylor, M. ; Suero, M. G. ; Gaunt, M. J. J. Am. Chem. Soc. 2014, 136, 8851.
28. [28]
  (a) Aradi, K. ; Bombicz, P. ; Novák, Z. J. Org. Chem. 2016, 81, 920.
  (b) Wen, R. -L. ; Dou, Q. ; Wang, Y. -C. ; Zhang, J. -W. ; Guo, W. -S. ; Li, M. J. Org. Chem. 2017, 82, 1428.
  (c) Wen, R. -L. ; Shen, Q. -Y. ; Guo, W. -S. ; Li, M. Org. Chem. Front. 2016, 3, 870.
  (d) Chi, Y. ; Yan, H. ; Zhang, W. -X. ; Xi, Z. Org. Lett. 2017, 19, 2694.
29. [29]
  (a) Chi, Y. ; Yan, H. ; Zhang, W. -X. ; Xi, Z. Org. Lett. 2017, 19, 2694.
  (b) Oh, K. H. ; Kim, J. G. ; Park, J. K. Org. Lett. 2017, 19, 3994.
30. [30]
  Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156. doi: 10.1021/jo501334u
31. [31]
  Xiang, S.-K.; Li, J.-M.; Huang, H.; Feng, C.; Ni, H.-L.; Chen, X.-Z.; Wang, B.-Q.; Zhao, K.-Q.; Hu, P.; Redshaw, C. Adv. Synth. Catal. 2015, 357, 3435. doi: 10.1002/adsc.201500651
32. [32]
  (a) Beringer, F. M. ; Gindler, E. M. J. Am. Chem. Soc. 1955, 77, 3203.
  (b) Caserio, M. C. ; Glusker, D. L. ; Roberts, J. D. J. Am. Chem. Soc. 1959, 81, 336.
33. [33]
  (a) Jalalian, N. ; Ishikawa, E. E. ; Silva, L. F. Jr. ; Olofson, B. Org. Lett. 2011, 13, 1552.
  (b) Jalalian, N. ; Petersen, T. B. ; Olofsson, B. Chem. Eur. J. 2012, 18, 14140.
  (c) Lindstedt, E. ; Ghosh, R. ; Olofsson, B. Org. Lett. 2013, 15, 6070.
  (d) Chan, L. ; McNally, A. ; Toh, Q. Y. ; Mendoza, A. ; Gaunt, M. J. Chem. Sci. 2015, 6, 1277.
34. [34]
  Thorat, P. B.; Waghmode, N. A.; Karade, N. N. Tetrahedron Lett. 2014, 55, 5718. doi: 10.1016/j.tetlet.2014.08.079
35. [35]
  (a) Lubinovski, J. J. ; Knapczyk, J. W. ; Calderon, J. L. ; Petit, L. R. ; McEwen, W. E. J. Org. Chem. 1975, 40, 3010.
  (b) Ghosh, R. ; Lindstedt, E. ; Jalalian, N. ; Olofsson, B. ChemistryOpen 2014, 3, 54.
36. [36]
  Sundalam, S. K.; Stuart, D. R. J. Org. Chem. 2015, 80, 6456. doi: 10.1021/acs.joc.5b00907
37. [37]
  Tolnai, G. L.; Nilsson, U. J.; Olofsson, B. Angew. Chem., Int. Ed. 2016, 55, 11226. doi: 10.1002/anie.201605999
38. [38]
  Kumar, D.; Arun, V.; Pilania, M.; Shekar, K. P. C. Synlett 2013, 24, 831. doi: 10.1055/s-00000083
39. [39]
  Xiong, B.; Feng, X.; Zhu, L.; Chen, T.; Zhou, Y.; Au, C.-T.; Yin, S.-F. ACS Catal. 2015, 5, 537. doi: 10.1021/cs501523g
40. [40]
  Bhattarai, B.; Tay, J.-H.; Nagorny, P. Chem. Commun. 2015, 51, 5398. doi: 10.1039/C4CC08604J
41. [41]
  Sandin, R. B.; Christiansen, R. G.; Brown, R. K.; Kirkwood, S. J. Am. Chem. Soc. 1947, 69, 1550.
42. [42]
  Huang, X.; Zhu, Q.; Xu, Y. Synth. Commun. 2001, 31, 2823. doi: 10.1081/SCC-100105332
43. [43]
  Krief, A.; Dumont, W.; Robert, M. Synlett 2006, 484.
44. [44]
  Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263. doi: 10.1021/jo402567b
45. [45]
  Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78, 12194. doi: 10.1021/jo401868x
46. [46]
  Saravanan, P.; Anbarasan, P. Adv. Synth. Catal. 2015, 357, 3521. doi: 10.1002/adsc.201500606
47. [47]
  Nikolaienko, P.; Yildiz, T.; Rueping, M. Eur. J. Org. Chem. 2016, 1091.
48. [48]
  Xu, J.; Zhang, P. B.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176. doi: 10.1021/jo4012199
49. [49]
  Miralles, N.; Romero, R. M.; Fernandez, E.; Muniz, K. Chem. Commun. 2015, 51, 14068. doi: 10.1039/C5CC04944J
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