Chinese Journal of Organic Chemistry >
Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom
Received date: 2018-02-22
Revised date: 2018-04-02
Online published: 2018-04-13
Supported by
Project supported by the Maoming City Technology Bureau (No. 917313), the Guangdong University of Petrochemical Technology (Nos. 517152, 517136, 2017pyA006).
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.
Key words： acyclic diaryl iodonium salt; heteroatom; arylation
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
[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] (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] Hartmann, C.; Meyer, V. Ber. Dtsch. Chem. Ges. 1894, 27, 426.
[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] (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] (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] (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] 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.
[9] Chun, J.-H.; Pike, V. W. Org. Biomol. Chem. 2013, 11, 6300.
[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] Carrol, M. A.; Wood, R. A. Tetrahedron 2007, 63, 11349.
[12] Sandtorv, A. H.; Stuart, D. R. Angew. Chem., Int. Ed. 2016, 55, 15812.
[13] Yang, Y.; Wu, X.; Han, J.; Mao, S.; Qian, X.; Wang, L. Eur. J. Org. Chem. 2014, 6854.
[14] Riedmüller, S.; Nachtsheim, B. J. Synlett 2015, 26, 651.
[15] Pang, X.; Lou, Z.; Li, M.; Wen, L.; Chen, C. Eur. J. Org. Chem. 2015, 3361.
[16] Geng, X.; Mao, S.; Chen, L.; Yu, J.; Han, J.; Hua, J.; Wang, L. Tetrahedron Lett. 2014, 55, 3856.
[17] Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.; Olofsson, B. Org. Lett. 2015, 17, 2688.
[18] Lucchetti, N.; Scalone, M.; Fantasia, S.; Muiz, K. Angew. Chem., Int. Ed. 2016, 55, 13335.
[19] Yang, Q.; He, X.-X.; Chang, J.; Wu, Q.; Zhang, B.-X. Chin. J. Org. Chem. 2011, 31, 1687 (in Chinese).
(杨祺, 和潇夏, 常姣, 吴群, 张变香. 有机化学, 2011, 31, 1687.)
[20] Guo, F.; Wang, L.; Wang, P.; Yu, J.; Han, J. Asian J. Org. Chem. 2012, 1, 218.
[21] Gonda, Zs.; Novák, Z. Chem. Eur. J. 2015, 21, 16801.
[22] Modha, S. G.; Greaney, M. F. J. Am. Chem. Soc. 2015, 137, 1416.
[23] Reitti, M.; Villo, P.; Olofsson, B. Angew. Chem. Int. Ed. 2016, 55, 8928.
[24] Li, X.; Li, L.; Mo, X.; Mo, D. Synth. Commun. 2016, 46, 963.
[25] Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323.
[26] Su, X.; Chen, C.; Wang, Y.; Chen, J.; Lou, Z.; Li, M. Chem. Commun. 2013, 49, 6752.
[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] (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] (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] Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156.
[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.
[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] (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] Thorat, P. B.; Waghmode, N. A.; Karade, N. N. Tetrahedron Lett. 2014, 55, 5718.
[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] Sundalam, S. K.; Stuart, D. R. J. Org. Chem. 2015, 80, 6456.
[37] Tolnai, G. L.; Nilsson, U. J.; Olofsson, B. Angew. Chem., Int. Ed. 2016, 55, 11226.
[38] Kumar, D.; Arun, V.; Pilania, M.; Shekar, K. P. C. Synlett 2013, 24, 831.
[39] Xiong, B.; Feng, X.; Zhu, L.; Chen, T.; Zhou, Y.; Au, C.-T.; Yin, S.-F. ACS Catal. 2015, 5, 537.
[40] Bhattarai, B.; Tay, J.-H.; Nagorny, P. Chem. Commun. 2015, 51, 5398.
[41] Sandin, R. B.; Christiansen, R. G.; Brown, R. K.; Kirkwood, S. J. Am. Chem. Soc. 1947, 69, 1550.
[42] Huang, X.; Zhu, Q.; Xu, Y. Synth. Commun. 2001, 31, 2823.
[43] Krief, A.; Dumont, W.; Robert, M. Synlett 2006, 484.
[44] Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263.
[45] Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78, 12194.
[46] Saravanan, P.; Anbarasan, P. Adv. Synth. Catal. 2015, 357, 3521.
[47] Nikolaienko, P.; Yildiz, T.; Rueping, M. Eur. J. Org. Chem. 2016, 1091.
[48] Xu, J.; Zhang, P. B.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176.
[49] Miralles, N.; Romero, R. M.; Fernandez, E.; Muniz, K. Chem. Commun. 2015, 51, 14068.
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