The review is devoted to one of the most substantial trends in the chemistry of hypervalent iodine – synthesis, structure, and properties of heterocyclic and pseudoheterocyclic systems based on λ3- and λ5-iodanes. Among the variety of cyclic reagents based on hypervalent iodine, special attention has recently been paid to iodanes having close contact between I and N atoms. The review is addressing the synthetic approaches, structural features, and application of these reagents. The review includes more than 100 literature sources, mainly covering publications from 1990 to 2020 and key research from earlier years.
Similar content being viewed by others
References
(a) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. (b) Zhdankin, V. V. ARKIVOC 2020. DOI: https://doi.org/10.24820/ark.5550190.p011.145. (c) Hypervalent Iodine Chemistry; Wirth, T., Ed.; Springer, 2016. (d) The Chemistry of Hypervalent Halogen Compounds; Olofsson, B.; Marek, I.; Rappoport, Z., Eds.; John Wiley & Sons, Ltd.: Chichester, 2019. (e) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Application of Polyvalent Iodine Compounds; John Wiley & Sons, Ltd.: Chichester, 2014. (f) Yusubov, M. S.; Zhdankin, V. V. Resour.-Effic. Technol. 2015, 1, 49.
(a) Chen, W. W.; Cuenca, A. B.; Shafir, A. Angew. Chem., Int. Ed. 2020. DOI: https://doi.org/10.1002/anie.201908418. (b) Yoshimura, A.; Saito, A.; Zhdankin, V. V. Chem.–Eur. J. 2018, 24, 15156. (c) Hari, D. P.; Caramenti, P.; Waser, J. Acc. Chem. Res. 2018, 51, 3212. (d) Ghosh, M. K.; Rajkiewicz, A. A.; Kalek, M. Synthesis 2019, 359. (e) Flores, A.; Cots, E.; Bergès, J.; Muñiz, K. Adv. Synth. Catal. 2019, 361, 2. (f) Hyatt, I. F. D.; Dave, L.; David, N.; Kaur, K.; Medard, M.; Mowdawalla, C. Org. Biomol. Chem. 2019, 17, 7822.
(a) Scilabra, P.; Terraneo, G.; Resnati, G. Acc. Chem. Res. 2019, 52, 1313. (b) Sreenithya, A.; Sunoj, R. B. Dalton Trans. 2019, 4086. (c) Grelier, G.; Darses, B.; Dauban, P. Beilstein J. Org. Chem. 2018, 14, 1508. (d) Boelke, A.; Finkbeiner, P.; Nachtsheim, B. J. Beilstein J. Org. Chem. 2018, 14, 1263.
(a) Richter, H. W.; Koser, G. F.; Incarvito, C. D.; Rheingold, A. L. Inorg. Chem. 2007, 46, 5555. (b) Yusubov, M. S.; Postnikov, P. S.; Yoshimura, A.; Zhdankin, V. V. Synlett 2020, 315. (c) Yannacone, S.; Oliveira, V.; Verma, N.; Kraka, E. Inorganics 2019, 7, 47. (d) Bauzá, A.; Quiñonero, D.; Frontera, A. Molecules 2018, 23, 18. (e) Pinto de Magalhães, H.; Togni, A.; Lüthi, H. P. J. Org. Chem. 2017, 82, 11799.
Justik, M. W.; Protasiewicz, J. D.; Updegraff, J. B. Tetrahedron Lett. 2009, 50, 6072.
Yoshimura, A.; Fuchs, J. M.; Middleton, K. R.; Maskaev, A. V.; Rohde, G. T.; Saito, A.; Postnikov, P. S.; Yusubov, M. S.; Nemykin, V. N.; Zhdankin, V. V. Chem.–Eur. J. 2017, 23, 16738.
Yoshimura, A.; Klasen, S. C.; Shea, M. T.; Nguyen, K. C.; Rohde, G. T.; Saito, A.; Postnikov, P. S.; Yusubov, M. S.; Nemykin, V. N.; Zhdankin, V. V. Chem –Eur. J. 2017, 23, 691.
(a) Legault, C. Y.; Prévost, J. Acta Crystallogr., Sect. E: Struct. Rep. Online 2012, E68, o1238. (b) Geary, G. C.; Hope, E. G.; Singh, K.; Stuart, A. M. Chem. Commun. 2013, 9263.
(a) Braddock, D. C.; Cansell, G.; Hermitage, S. A.; White, A. J. P. Chem. Commun. 2006, 1442. (b) Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192. (c) Eisenberger, P.; Gischig, S.; Togni, A. Chem.–Eur. J. 2006, 12, 2579.
Koser, G. F.; Sun, G.; Porter, C. W.; Youngs, W. J. J. Org. Chem. 1993, 58, 7310.
Nemykin, V. N.; Maskaev, A. V.; Geraskina, M. R.; Yusubov, M. S.; Zhdankin, V. V. Inorg. Chem. 2011, 50, 11263.
Kraszkiewicz, L.; Skulski, L. ARKIVOC 2003, (vi), 120.
(a) Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Formaneck, M. S.; Bolz, J. T. Tetrahedron Lett. 1994, 35, 9677. (b) Vita, M. V.; Waser, J. Org. Lett. 2013, 15, 3246.
(a) Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Mismash, B.; Woodward, J. K.; Simonsen, A. J. Tetrahedron Lett. 1995, 36, 7975. (b) Shen, H.; Li, J.; Liu, Q.; Pan, J.; Huang, R.; Xiong, Y. J. Org. Chem. 2015, 80, 7212.
Matoušek, V.; Václavík, J.; Hájek, P.; Charpentier, J.; Blastik, Z. E.; Pietrasiak, E.; Budinská, A.; Togni, A.; Beier, P. Chem.–Eur. J. 2016, 22, 417.
Matoušek, V.; Pietrasiak, E.; Schwenk, R.; Togni, A. J. Org. Chem. 2013, 78, 6763.
Zhdankin, V. V.; Litvinov, D. N.; Koposov, A. Y.; Luu, T.; Ferguson, M. J.; McDonald, R.; Tykwinski, R. R. Chem. Commun. 2004, 106.
Meprathu, B. V.; Justik, M. W.; Protasiewicz, J. D. Tetrahedron Lett. 2005, 46, 5187.
Macikenas, D.; Skrzypczak-Jankun, E.; Protasiewicz, J. D. Angew. Chem., Int. Ed. 2000, 39, 2007.
Yusubov, M. S.; Soldatova, N. S.; Postnikov, P. S.; Valiev, R. R.; Yoshimura, A.; Wirth, T.; Nemykin, V. N.; Zhdankin, V. V. Chem. Commun. 2019, 7760.
Hartman, C.; Mayer, V. Ber. Dtsch. Chem. Ges. 1893, 26, 1727.
Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
(а) Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251. (b) Mironova, I. A.; Postnikov, P. S.; Yusubova, R. Y.; Yoshimura, A.; Wirth, T.; Zhdankin, V. V.; Nemykin, V. N.; Yusubov, M. S. Beilstein J. Org. Chem. 2018, 14, 1854. (с) Koposov, A. Y.; Litvinov, D. N.; Zhdankin, V. V.; Ferguson, M. J.; McDonald, R.; Tykwinski, R. R. Eur. J. Org. Chem. 2006, 4791.
Yusubov, M. S.; Svitich, D. Y.; Yoshimura, A.; Nemykin, V. N.; Zhdankin, V. V. Chem. Commun. 2013, 49, 11269.
Veretennikov, E. A.; Gavrilov, A. E. Chem. Heterocycl. Compd. 2007, 43, 1081. [Khim. Geterotsikl. Soedin. 2007, 1273.]
(a) Lishchynskyi, A.; Muñiz, K. Chem.–Eur. J. 2012, 18, 2212. (b) Souto, J. A.; Becker, P.; Iglesias, A.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 15505. (c) Souto, J. A.; Zian, D.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 7242.
Röben, C.; Souto, J. A.; Escudero-Adán, E. C.; Muñiz, K. Org. Lett. 2013, 15, 1008.
(a) Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Synthesis 1983, 207. (b) Papadopoulou, M.; Varvoglis, A. J. Chem. Res., Synop. 1983, 66. (c) Papadopoulou, M.; Varvoglis, A. J. Chem. Res., Synop. 1984, 166. (d) Souto, J. A.; González, Y.; Iglesias, A.; Zian, D.; Lishchynskyi, A.; Muñiz, K. Chem.–Asian J. 2012, 7, 1103. (e) Kantak, A. A.; Marchetti, L.; DeBoef, B. Chem. Commun. 2015, 3574.
(a) Souto, J. A.; Martínez, C.; Velilla, I.; Muñiz, K. Angew. Chem., Int. Ed. 2013, 52, 1324. (b) Yoshimura, A.; Koski, S. R.; Fuchs, J. M.; Saito, A.; Nemykin, V. N.; Zhdankin, V. V. Chem.–Eur. J. 2015, 21, 5328.
(a) Han, H.; Tsarevsky, N. V. Chem. Sci. 2014, 5, 4599. (b) Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406.
(a) Lazbin, I. M.; Koser, G. F. J. Org. Chem. 1987, 52, 476. (b) Koser, G. F.; Kokil, P. B.; Shah, M. Tetrahedron Lett. 1987, 28, 5431.
Mikhael, M.; Adler, S. A.; Wengryniuk, S. E. Org. Lett. 2019, 21, 5889.
Montanari, V.; DesMarteau, D. D.; Pennington, W. T. J. Mol. Struct. 2000, 550 −551, 337.
Postnikov, P. S.; Guselnikova, O. A.; Yusubov, M. S.; Yoshimura, A.; Nemykin, V. N.; Zhdankin, V. V. J. Org. Chem. 2015, 80, 5783.
(a) Ishida, K.; Togo, H. Moriyama, K. Chem.–Asian J. 2016, 11, 3583. (b) Moriyama, K.; Ishida, K.; Togo, H. Chem. Commun. 2015, 51, 2273.
(a) Marchetti, L.; Kantak, A.; Davis, R.; DeBoef, B. Org. Lett. 2015, 17, 358. (b) Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996. (c) Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382. (d) Röben, C.; Souto, J. A.; González, Y.; Lishchynskyi, A.; Muñiz, K. Angew. Chem., Int. Ed. 2011, 50, 9478. (e) Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436. (f) Galligan, M. J.; Akula, R.; Ibrahim, H. Org. Lett. 2014, 16, 600. (g) Xu, L.; Mou, X.-Q.; Chen, Z.-M.; Wang, S.-H. Chem. Commun. 2014, 50, 10676. h Pedersen, C. M.; Marinescu, L. G.; Bols, M. Org. Biomol. Chem. 2005, 3, 816. (h) Xie, F.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2013, 52, 11862.
Ochiai, M.; Nakano, A.; Yoshimura, A.; Miyamoto, K.; Hayashi, S.; Nakanishi, W. Chem. Commun. 2009, 959.
Kobayashi, Y.; Masakado, S.; Takemoto, Y. Angew. Chem., Int. Ed. 2018, 57, 693.
Ochiai, M.; Nakano, A.; Yoshimura, A.; Miyamoto, K.; Hayashi, S.; Nakanishi, W. Chem. Commun. 2009, 959.
Macikenas, D.; Skrzypczak-Jankun, E.; Protasiewicz, J. D. J. Am. Chem. Soc. 1999, 121, 7164.
Jaffe, H.; Leffler, J. E. J. Org. Chem. 1975, 40, 797.
(a) Balthazor, T. M.; Godar, D. E.; Stults, B. R. J. Org. Chem. 1979, 44, 1447. (b) Wolf, W.; Steinberg, L. Chem. Commun. (London) 1965, 449. (c) Barber, H. J.; Henderson, M. A. J. Chem. Soc. C. 1970, 862.
Boelke, A.; Vlasenko, Y. A.; Yusubov, M. S.; Nachtsheim, B. J.; Postnikov, P. S. Beilstein J. Org. Chem. 2019, 15, 2311.
(a) Zhdankin, V. V.; Arbit, R. M.; McSherry, M.; Mismash, B.; Young, V. G. J. Am. Chem. Soc. 1997, 119, 7408. (b) Zhdankin, V. V.; Arbit, R. M.; Lynch, B.; Kiprof, P.; Young, V. G. J. Org. Chem. 1998, 63, 6590.
Zhdankin, V. V.; Koposov, A. Y.; Su, L.; Boyarskikh, V. V.; Netzel, B. C.; Young, V. G. Org. Lett. 2003, 5, 1583.
(a) Zhdankin, V. V.; Koposov, A. E.; Smart, J. T.; Tykwinski, R. R.; McDonald, R.; Morales-Izquierdo, A. J. Am. Chem. Soc. 2001, 123, 4095. (b) Kiprof, P.; Zhdankin, V. V. ARKIVOC 2003, (vi), 170.
Yoshimura, A.; Shea, M. T.; Makitalo, C. D.; Jarvi, M. E.; Rohde, G. T.; Saito, A.; Yusubov, M. S.; Zhdankin, V. V. Beilstein J. Org. Chem. 2018, 14, 1016.
Yang, X.-G.; Zheng, K.; Zhang, C. Org. Lett. 2020, 22, 2026.
Aertker, K.; Rama, R. J.; Opalach, J.; Muñiz, K. Adv. Synth. Catal. 2017, 359, 1290.
Boelke, A.; Lork, E.; Nachtsheim, B. J. Chem.–Eur. J. 2018, 24, 18653.
Vlasenko, Y. A.; Postnikov, P. S.; Trusova, M. E.; Shafir, A.; Zhdankin, V. V.; Yoshimura, A.; Yusubov, M. S. J. Org. Chem. 2018, 83, 12056.
Moss, R. A.; Chatterjee, S.; Wilk, B. J. Org. Chem. 1986, 51, 4303.
(a) Guilbault, A.-A.; Legault C. Y. ACS Catal. 2012, 2, 219. (b) Guilbault, A.-A.; Basdevant, B.; Wanie, V.; Legault, C. Y. J. Org. Chem. 2012, 77, 11283. (c) Thérien, M.-È.; Guilbault, A.-A.; Legault, C. Y. Tetrahedron: Asymmetry 2013, 24, 1193.
(a) Boelke, A.; Nachtsheim, B. J. Adv. Synth. Catal. 2020, 362, 184.(b) Abazid, A. H.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2020, 59, 1479.
Rodríguez, A.; Moran, W. J. Synthesis 2012, 1178.
(a) Levitre, G.; Dumoulin, A.; Retailleau, P.; Panossian, A.; Leroux, F. R.; Masson, G. J. Org. Chem. 2017, 82, 11877. (b) Bekkaye, M.; Masson, G. Synthesis 2016, 302.
(a) Li, X.; Chen, P.; Liu, G. Beilstein J. Org. Chem. 2018, 14, 1813.(b) Muñiz, K. Acc. Chem. Res. 2018, 51, 1507. (c) Romero, R. M.; Wöste, T. H.; Muñiz, K. Chem.–Asian J. 2014, 9, 972. (d) Lee, J. H.; Choi, S.; Hong, K. B. Molecules 2019, 24, 2634.
Mizar, P.; Laverny, A.; El-Sherbini, M.; Farid, U.; Brown, M.; Malmedy, F.; Wirth, T. Chem.–Eur. J. 2014, 20, 9910.
Hempel, C.; Maichle-Mössmer, C.; Pericàs, M. A.; Nachtsheim, B. J. Adv. Synth. Catal. 2017, 359, 2931.
Vaish, A.; Sayala, K. D.; Tsarevsky, N. V. Tetrahedron Lett. 2019, 60, 150995.
(a) Shao, X.; Wang, X.; Yang, T.; Lu, L; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457. (b) Vinogradova, E. V.; Müller, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2014, 53, 3125.
Cao, Y.; Kumar, R.; Tsarevsky, N. V. Macromol. Chem. Phys. 2019, 220, 1800471.
(a) Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285. (b) Usui, K.; Yamamoto, K.; Shimizu, T.; Okazumi, M.; Mei, B.; Demizu, Y.; Kurihara, M.; Suemune, H. J. Org. Chem. 2015, 80, 6502. (c) Yusubov, M. S.; Postnikov, P. S.; Yusubova, R. Y.; Yoshimura, A.; Jürjens, G.; Kirschning, A.; Zhdankin, V. V. Adv. Synth. Catal. 2017, 359, 3207. (d) Dess, D. B.; Wilson, S. R.; Martin, J. C. J. Am. Chem. Soc. 1993, 115, 2488.
Zhdankin, V. V.; Smart, J. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299.
Zhdankin, V. V.; Koposov, A. Y.; Yashin, N. V. Tetrahedron Lett. 2002, 43, 5735.
Xiao, X.; Greenwood, N. S.; Wengryniuk, S. E. Angew. Chem., Int. Ed. 2019, 58, 16181.
Yakura, T.; Fujiwara, T.; Yamada, A.; Nambu, H. Beilstein J. Org. Chem. 2018, 14, 971.
The review was prepared with the financial support of the Russian Foundation for Basic Research (grant 19-43-703004).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 854–866
Rights and permissions
About this article
Cite this article
Vlasenko, Y.А., Yusubov, M.S., Shafir, A. et al. Hypervalent iodine in the structure of N-heterocycles: synthesis, structure, and application in organic synthesis. Chem Heterocycl Comp 56, 854–866 (2020). https://doi.org/10.1007/s10593-020-02742-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02742-0