Reviews

Progresses of Diaryliodonium Salts in Organic Reactions

  • Xiao Zhichao ,
  • Xia Chengfeng
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  • a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201;
    b University of Chinese Academy of Sciences, Beijing 100039

Received date: 2013-03-26

  Revised date: 2013-04-28

  Online published: 2013-05-09

Supported by

Project supported by the National Natural Science Foundation of China (No. 21072201) and the National Basic Research Program of China (973 Program, No. 2011CB915500).

Abstract

Diaryliodonium salts, a kind of mild, non-toxic and stable arylation reagent, have wide applications in organic chemistry. This review presents its structure and reaction activity characteristics, preparation methods, recent progresses in arylation of C—H bond, arylation of carbonyl compounds, cascade reaction, as well as arylation of hetero-atom nucleophiles. The characteristics of the reaction mechanisms and their applications are also discussed.

Cite this article

Xiao Zhichao , Xia Chengfeng . Progresses of Diaryliodonium Salts in Organic Reactions[J]. Chinese Journal of Organic Chemistry, 2013 , 33(10) : 2119 -2130 . DOI: 10.6023/cjoc201303040

References

[1] Willgerodt, C. J. Prakt. Chem. 1886, 33, 154.
[2] Willgerodt, C. Ber. 1892, 25, 3494.
[3] Hartmann, C.; Meyer, V. Ber 1893, 26, 1727.
[4] Hartmann, C.; Meyer, V. Ber 1894, 27, 426.
[5] (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) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
[6] Beringer, F. M.; Brierley, A.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. J. Am. Chem. Soc. 1953, 75, 2708.
[7] Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.
[8] Ochiai, M. Top. Curr. Chem. 2003, 224, 5.
[9] Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Angew. Chem., Int. Ed. 2010, 49, 3334.
[10] (a) Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521;
(b) Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610.
[11] Bielawski, M.; Krämer, K.; Olofsson, B. Org. Synth 2009, 86, 308.
[12] Koser, G. F.; Wettach, R. H.; Smith, C. S. J. Org. Chem. 1980, 45, 1543.
[13] W. Pike, V.; Butt, F.; Shah, A.; Widdowson, D. J. Chem. Soc., Perkin Trans. 1 1999, 245.
[14] Ochiai, M.; Toyonari, M.; Sueda, T.; Kitagawa, Y. Tetrahedron Lett. 1996, 37, 8421.
[15] Bielawski, M.; Aili, D.; Olofsson, B. J. Org. Chem. 2008, 73, 4602.
[16] Cardinale, J.; Ermert, J.; Coenen, H. H. Tetrahedron 2012, 68, 4112.
[17] Dohi, T.; Yamaoka, N.; Kita, Y. Tetrahedron 2010, 66, 5775.
[18] Chun, J.-H.; Pike, V. W. J. Org. Chem. 2012, 77, 1931.
[19] Hirschberg, M. E.; Wenda, A.; Frohn, H.-J.; Ignatev, N. V. J. Fluorine Chem. 2012, 138, 24.
[20] Ito, M.; Itani, I.; Toyoda, Y.; Morimoto, K.; Dohi, T.; Kita, Y., Angew. Chem., Int. Ed. 2012, 51, 12555.
[21] Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. J. Am. Chem. Soc. 1999, 121, 9233.
[22] Jalalian, N.; Olofsson, B. Tetrahedron 2010, 66, 5793.
[23] Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
[24] Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
[25] Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234.
[26] (a) Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172;
(b) Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593.
[27] Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
[28] Chen, B.; Hou, X.-L.; Li, Y.-X.; Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 7668.
[29] Casitas, A.; Ribas, X. Chem. Sci. 2013, 4, 2301.
[30] Lockhart, T. P. J. Am. Chem. Soc. 1983, 105, 1940.
[31] Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463.
[32] Ciana, C. L.; Phipps, R. J.; Brandt, J. R.; Meyer, F. M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 458.
[33] Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552.
[34] Storr, T. E.; Greaney, M. F. Org. Lett. 2013, 15, 1410.
[35] Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773.
[36] Gigant, N.; Chausset-Boissarie, L.; Belhomme, M.-C.; Poisson, T.; Pannecoucke, X.; Gillaizeau, I. Org. Lett. 2012, 14, 278.
[37] Li, J.; Liu, L.; Zhou, Y.-Y.; Xu, S.-N. RSC Adv. 2012, 2, 3207.
[38] Vaddula, B. R.; Saha, A.; Leazer, J.; Varma, R. S. Green Chem. 2012, 14, 2133.
[39] Kita, Y.; Morimoto, K.; Ito, M.; Ogawa, C.; Goto, A.; Dohi, T. J. Am. Chem. Soc. 2009, 131, 1668.
[40] Ackermann, L.; Dell'Acqua, M.; Fenner, S.; Vicente, R. N.; Sandmann, R. Org. Lett. 2011, 13, 2358.
[41] Wen, J.; Zhang, R.-Y.; Chen, S.-Y.; Zhang, J.; Yu, X.-Q. J. Org. Chem. 2011, 77, 766.
[42] Castro, S.; Fernandez, J. J.; Vicente, R.; Fananas, F. J.; Rodriguez, F. Chem. Commun. 2012, 48, 9089.
[43] Marshall Beringer, F.; Forgione, P. S.; Yudis, M. D. Tetrahedron 1960, 8, 49.
[44] Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260.
[45] Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986.
[46] (a) Taylor, A. M.; Altman, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 9900.
(b) Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 195.
(c) Lundin, P. M.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11027.
[47] Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. J. Am. Chem. Soc. 2011, 133, 13782.
[48] Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778.
[49] Toh, Q. Y.; McNally, A.; Vera, S.; Erdmann, N.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 3772.
[50] Zhu, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 10815.
[51] Kieffer, M. E.; Chuang, K. V.; Reisman, S. E. Chem. Sci. 2012, 3, 3170.
[52] Liu, C.; Zhang, W.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 4525.
[53] Rousseaux, S.; Vrancken, E.; Campagne, J.-M. Angew. Chem., Int. Ed. 2012, 51, 10934.
[54] Pike, V. W.; Aigbirhio, F. I. J. Chem. Soc., Chem. Commun. 1995, 2215.
[55] Tredwell, M.; Gouverneur, V. Angew. Chem., Int. Ed. 2012, 51, 11426.
[56] Chun, J.-H.; Lu, S.; Lee, Y.-S.; Pike, V. W. J. Org. Chem 2010, 75, 3332.
[57] Ross, T. L.; Ermert, J.; Hocke, C.; Coenen, H. H. J. Am. Chem. Soc. 2007, 129, 8018.
[58] Niu, H.-Y.; Xia, C.; Qu, G.-R.; Zhang, Q.; Jiang, Y.; Mao, R.-Z.; Li, D.-Y.; Guo, H.-M. Org. Biomol. Chem. 2011, 9, 5039.
[59] Li, J.; Liu, L. RSC Adv. 2012, 2, 10485.
[60] Guo, F.; Wang, L.; Wang, P.; Yu, J.; Han, J. Asian J. Org. Chem. 2012, 1, 218.
[61] Vaddula, B.; Leazer, J.; Varma, R. S. Adv. Synth. Catal. 2012, 354, 986.
[62] Landge, K. P.; Jang, K. S.; Lee, S. Y.; Chi, D. Y. J. Org. Chem. 2012, 77, 5705.
[63] Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436.
[64] Crowder, J. R.; Glover, E. E.; Grundon, M. F.; Kaempfen, H. X. J. Chem. Soc. 1963, 4578.
[65] Petersen, T. B.; Khan, R.; Olofsson, B. Org. Lett. 2011, 13, 3462.
[66] Kuriyama, M.; Hamaguchi, N.; Onomura, O. Chem. Eur. J. 2012, 18, 1591.
[67] Umierski, N.; Manolikakes, G. Org. Lett. 2012, 14, 188.
[68] Bhong, B. Y.; Shelke, A. V.; Karade, N. N. Tetrahedron Lett. 2012, 54, 739.
[69] Norrby, P.-O.; Petersen, T. B.; Bielawski, M.; Olofsson, B. Chem. Eur. J. 2010, 16, 8251.
[70] (a) Aggarwal, V. K.; Olofsson, B. Angew. Chem., Int. Ed. 2005, 44, 5516;
(b) Silva Jr, L. F.; Olofsson, B. Nat. Prod. Rep. 2011, 28, 1722.
[71] Wang, B.; Graskemper, J. W.; Qin, L.; DiMagno, S. G. Angew. Chem., Int. Ed. 2010, 49, 4079.
[72] Trost, B. M. Science 1991, 254, 1471.
[73] Dohi, T.; Kita, Y. Chem. Commun. 2009, 2073.
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