The microreview covers three, most powerful, strategies of the synthesis of phosphinine (systematically called phosphabenzene) starting from pyrylium salts, five-membered heterocycles, and reagents with C≡P bond.
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References
Ashe, J. A. J. Am. Chem. Soc. 1971, 93, 3293.
Märkl, G. Angew. Chem. 1966, 78, 907.
Savateev, A.; Vlasenko, Y.; Shtil, N.; Kostyuk, A. Eur. J. Inorg. Chem. 2016, 628.
Nyulaszi, L. Chem. Rev. 2001, 101, 1229.
Weemers, J. J. M. Phosphinine-Based Ligands: Unique Phosphorus Heterocycles in Homogeneous Catalytic Reactions; Eindhoven: Technische Universiteit Eindhoven, 2014, DOI: https://doi.org/10.6100/IR762991.
Kostenko, N.; Ericsson, C.; Engqvist, E.; Gonzalez, S. V.; Bayer, A. Eur. J. Org. Chem. 2013, 4756.
Mastalir, M.; Kirchner, K. Monatsh. Chem. 2017, 148, 105.
Muller, C.; Broeckx, L. E. E.; de Krom, I.; Weemers, J. J. M. Eur. J. Inorg. Chem. 2013, 187.
(a) Müller, C.; Broeckx, L. E. E.; de Krom, I.; Weemers, J. J. M. Eur. J. Inorg. Chem. 2013, 187. (b) Corbridge, D. E. C. Phosphorus: Chemistry, Biochemistry, and Technology; Taylor & Francis, 2013, 6th ed.
Märkl, G. Angew. Chem., Int. Ed. 1967, 6, 944.
Van der Velde, N. A.; Korbitz, H. T.; Garner, C. M. Tetrahedron Lett. 2012, 53, 5742.
Muller, C.; Pidko, E. A.; Staring, A. J. P. M.; Lutz, M.; Spek, A. L.; Van Santen, R. A.; Vogt, D. Chem.–Eur. J. 2008, 14, 4899.
Muller, C.; Lopez, L. G.; Kooijman, H.; Spek, A. L.; Vogt, D. Tetrahedron Lett. 2006, 47, 2017.
Muller, C.; Wasserberg, D.; Weemers, J. J. M.; Pidko, E. A.; Hoffmann, S.; Lutz, M.; Spek, A. L.; Meskers, S. C. J.; Janssen, R. A. J.; Van Santen, R. A.; Vogt, D. Chem.–Eur. J. 2007, 13, 4548.
Nagahora, N.; Ogawa, T.; Honda, M.; Fujii, M.; Tokumaru, H.; Sasamori, T.; Shioji K.; Okuma, K. Chem. Lett. 2015, 44, 706.
Wrackmeyer, B.; Klaus, U. J. Organomet. Chem. 1996, 520, 211.
Hunter, R. A.; Whitby, R. J.; Light, M. E.; Hursthouse, M. B. Tetrahedron Lett. 2004, 45, 7633.
Mao, Y.; Mathey F. Chem.–Eur. J. 2011, 17, 10745.
Wang, H.; Li, C.; Geng, D.; Chen, H.; Duan, Z.; Mathey, F. Chem.–Eur. J. 2010, 16, 10659.
Grundy, J.; Mathey, F. Angew. Chem., Int. Ed. 2005, 44, 1082.
(a) Rösch, W.; Regitz, M. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1986, 41, 931. (b) Habicht, M. H.; Wossidlo, F.; Weber, M.; Muller, C. Chem.–Eur. J. 2016, 22, 12877.
Chen, X.; Alidori, S.; Puschmann, F. F.; Santiso-Quinones, G.; Benko, Z.; Li, Z.; Becker, G.; Grutzmacher, H.-F.; Grutzmacher, H. Angew. Chem., Int. Ed. 2014, 53, 1641.
(a) Nakajima, K.; Takata, S.; Sakata, K.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2015, 54, 7597. (b) Nakajima, K.; Liang, W.; Nishibayashi, Y. Org. Lett. 2016, 18, 5006.
Financial support by Polish National Science Centre (UMO-2014/13/N/ST5/01532) is gratefully acknowledged.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 858–860
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Tokarz, P., Zagórski, P.M. Phosphinine – synthesis of a heavy sibling of pyridine (microreview). Chem Heterocycl Comp 53, 858–860 (2017). https://doi.org/10.1007/s10593-017-2138-1
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DOI: https://doi.org/10.1007/s10593-017-2138-1