Abstract
Over the past decades, the pincer ligands have attracted an increasing interest due to the unique properties of the coordination compounds they form. These monoanionic tridentate ligands are of great importance in organometallic and coordination chemistry. Their complexes with transition metals are used as homogeneous catalysts for various processes and also as functional materials with specified properties. The metal complexes formed by the pincer ligands provide an efficient alternative to the existing catalysts based on noble metals and, hence, the use of these complexes is a promising task of the modern chemical science. Therefore, nickel as the most accessible and inexpensive analog of palladium and platinum is of great practical interest. In this review, we consider the diversity of nickel complexes with pincer ligands, as well as the existing methods for their preparation and practical application.
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References
G. W. Parshall, Acc. Chem. Res., 1970, 3, 139.
J. Dehand, M. Pfeffer, Coord. Chem. Rev., 1976, 18, 327.
A. E. Shilov, G. B. Shulpin, Chem. Rev., 1997, 97, 2897.
G. van Koten, Pure Appl. Chem., 1989, 61, 1681.
M. Albrecht, G. van Koten, Angew. Chem., Int. Ed., 2001, 40, 3750.
M. Gandelman, A. Vigalok, L. J. W. Shimon, D. Milstein, Organometallics, 1997, 16, 3981.
M. Mehring, M. Schürmann, K. Jurkschat, Organometallics, 1998, 17, 1227.
J. Vicente, A. Arcas, M.-A. Blasco, J. Lozano, M. C. Ramírez de Arellano, Organometallics, 1998, 17, 5374.
D. Morales-Morales, C. M. Jensen, The Chemistry ofPincer Compounds, Elsevier, Amsterdam, 2007.
R. A. Gossage, L. A. van de Kuil, G. van Koten, Acc. Chem. Res., 1998, 31, 423.
M. E. van der Boom, D. Milstein, Chem. Rev., 2003, 103, 1759.aa
J. T. Singleton, Tetrahedron, 2003, 59, 1837.
D. Morales-Morales, Rev. Soc. Quím. Méx., 2004, 48, 338.aaaaaa
E. Peris, R. H. Crabtree, Coord. Chem. Rev., 2004, 248, 2239.aaa
L.-C. Liang, Coord. Chem. Rev., 2006, 250, 1152.
H. Nishiyama, Chem. Soc. Rev., 2007, 36, 1133.
D. Pugh, A. A. Danopoulos, Coord. Chem. Rev., 2007, 251, 610.
D. Morales-Morales, Mini-Rev. Org. Chem., 2008, 5, 141.
W. Leis, H. A. Mayer, W. C. Kaska, Coord. Chem. Rev., 2008, 252, 1787.
D. Benito-Garagorri, K. Kirchner, Acc. Chem. Res., 2008, 41, 201.
H. Nishiyama, J. Ito, Chem. Commun., 2010, 46, 203.
J. Choi, A. H. R. MacArthur, M. Brookhart, A. S. Goldman, Chem. Rev., 2011, 111, 1761.
N. Selander, K. J. Szabó, Chem. Rev., 2011, 111, 2048.
K. J. Szabo, O. F. Wendt, Pincer and Pincer-Type Complexes, Wiley-VCH, Weinheim, 2014.
R. M. Bullock, Catalysis without Precious Metals, Wiley-VCH, Weinheim, 2010.
A. A. Kulkarni, O. Daugulis, Synthesis, 2009, 4087.
S. Chakraborty, H. Guan, Dalton Trans., 2010, 39, 7427.
Y. Tamaru, Modern OrganonickelChemistry, Wiley-VCH, Weinheim, Germany, 2005.
J. Campora, in Comprehensive Organometallic Chemistry III, Eds R. H. Crabtree, D. M. P. Mingos, Elsevier, Oxford, 2007, Vol. 8 (Compounds ofGroup 10), pp. 27–132.
D. G. Yakhvarov, E. A. Trofimova, I. Kh. Rizvanov, O. S. Fomina, O. G. Sinyashin, Russ. J. Electrochem., 2011, 47, 1100.
I. F. Sakhapov, Z. N. Gafurov, V. M. Babaev, I. Kh. Rizvanov, A. B. Dobrynin, D. B. Krivolapov, Kh. R. Khayarov, O. G. Sinyashin, D. G. Yakhvarov, Mendeleev Commun., 2016, 26, 131.
I. F. Sakhapov, Z. N. Gafurov, V. M. Babaev, V. A. Kurmaz, R. R. Mukhametbareev, I. Kh. Rizvanov, O. G. Sinyashin, D. G. Yakhvarov, Russ. J. Electrochem., 2015, 51, 1061.
Z. N. Gafurov, L. I. Musin, I. F. Sakhapov, V. M. Babaev, E. I. Musina, A. A. Karasik, O. G. Sinyashin, D. G. Yakhvarov, Phosphorus, Sulfur Silicon Relat. Elem., 2016, 191, 1475.
Z. N. Gafurov, O. G. Sinyashin, D. G. Yakhvarov, Pure Appl. Chem., 2017, 89, 1089.
Z. N. Gafurov, I. F. Sakhapov, V. M. Babaev, A. B. Dobrynin, V. A. Kurmaz, K. E. Metlushka, I. K. Rizvanov, G. R. Shaikhutdinova, O. G. Sinyashin, D. G. Yakhvarov, Russ. Chem. Bull., 2017, 66, 254.
Z. N. Gafurov, A. O. Kantyukov, A. A. Kagilev, A. A. Balabayev, O. G. Sinyashin, D. G. Yakhvarov, Russ. Chem. Bull., 2017, 66, 1529.
C. J. Moulton, B. L. Shaw, J. Chem. Soc., Dalton Trans., 1976, 1020.
V. A. Levina, A. Rossin, N. V. Belkova, M. R. Chierotti, L. M. Epstein, O. A. Filippov, R. Gobetto, L. Gonsalvi, A. Lledós, E. S. Shubina, F. Zanobini, M. Peruzzini, Angew. Chem., Int. Ed., 2011, 50, 1367.
K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, G. K. Fukin, G. A. Abakumov, Dalton Trans., 2004, 2957.
K. A. Kozhanov, M. P. Bubnov, N. N. Vavilina, L. Y. Efremova, G. K. Fukin, V. K. Cherkasov, G. A. Abakumov, Polyhedron, 2009, 28, 2555.
A. G. Starikov, R. M. Minyaev, K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, G. A. Abakumov, Russ. Chem. Bull., 2010, 59, 1110.
K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, N. N. Vavilina, L. Y. Efremova, O. I. Artyushin, I. L. Odinets, G. A. Abakumov, Dalton Trans., 2008, 2849.
K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, G. K. Fukin, G. A. Abakumov, Chem. Commun., 2003, 2610.
J. Cámpora, P. Palma, D. delRío, E. Álvarez, Organome tallics, 2004, 23, 1652.
J. Cámpora, P. Palma, D. delRío, M. M. Conejo, E. Álvarez, Organometallics, 2004, 23, 5653.
B. J. Boro, E. N. Duesler, K. I. Goldberg, R. A. Kemp, Inorg. Chem., 2009, 48, 5081.
B. J. Boro, D. A. Dickie, K. I. Goldberg, R. A. Kemp, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2008, 64. m1304.
B. J. Boro, D. A. Dickie, E. N. Duesler, K. I. Goldberg, R. A. Kemp, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2008, 64. m1402.
V. Boris, L. Fabien, D. Zargarian, Green Chem., 2013, 15, 3188.
J. Jonasson, O. F. Wendt, J. Organomet. Chem., 2014, 759, 15.
K. J. Jonasson, O. F. Wendt, Chem. Eur. J., 2014, 20, 11894.
J. Borau-Garcia, D. Gutsulyak, R. Burford, W. Piers, Dalton Trans., 2015, 44, 12082.
S. Murugesan, B. Stoeger, M. D. Carvalho, L. P. Ferreira, E. Pittenauer, G. Allmaier, L. F. Veiros, K. Kirchner, Organometallics, 2014, 33, 6132.
S. Murugesan, B. Stoeger, M. Weil, L. F. Veiros, K. Kirchner, Organometallics, 2015, 35, 1364.
D. G. Gusev, A. J. Lough, Organometallics, 2002, 21, 5091.
H. Rimml, L. M. Venanzi, J. Organomet. Chem., 1983, 259. C6.
M. T. Johnson, O. F. Wendt, Inorg. Chim. Acta, 2011, 367, 222.
H. Rimml, L. M. Venanzi, J. Organomet. Chem., 1984, 260. C52.
A. R. Kennedy, R. J. Cross, K. W. Muir, Inorg. Chim. Acta, 1995, 231, 195.
L. F. Groux, F. Bélanger-Gariépy, D. Zargarian, Can. J. Chem., 2005, 83, 634.
C.-C. Liu, Q.-L. Liu, Z.-Y. Wu, Y.-C. Chen, H.-J. Xie, J. Mol. Model., 2015, 21, 242.
M. E. van der Boom, S.-Y. Liou, L. J. W. Shimon, Y. Ben-David, D. Milstein, Inorg. Chim. Acta, 2004, 357, 4015.
A. Castonguay, C. Sui-Seng, D. Zargarian, A. L. Beauchamp, Organometallics, 2006, 25, 602.
A. Castonguay, D. Zargarian, A. L. Beauchamp, Organo metallics, 2008, 27, 5723.
A. Castonguay, A. L. Beauchamp, D. Zargarian, Inorg. Chem., 2009, 48, 3177.
V. Gómez-Benítez, O. Baldovino-Pantaleón, C. HerreraÁlvarez, R. A. Toscano, D. Morales-Morales, Tetrahedron Lett., 2006, 47, 5059.
V. Pandarus, D. Zargarian, Chem. Commun., 2007, 978.
V. Pandarus, D. Zargarian, Organometallics, 2007, 26, 4321.
A. Salah, D. Zargarian, Dalton Trans., 2011, 40, 8977.
S. Chakraborty, J. A. Krause, H. Guan, Organometallics, 2009, 28, 582.
J. Zhang, C. M. Medley, J. A. Krause, H. Guan, Organometallics, 2010, 29, 6393.
S. Chakraborty, Y. J. Patel, J. A. Krause, H. Guan, Polyhedron, 2012, 32, 30.
X. Lefévre, D. M. Spasyuk, D. Zargarian, J. Organomet. Chem., 2011, 696, 864.
A. Salah, C. Offenstein, D. Zargarian, Organometallics, 2011, 30, 5352.
S. Chakraborty, J. Zhang, J. A. Krause, H. Guan, J. Am. Chem. Soc., 2010, 132, 8872.
A. Salah, M. Corpet, N. ul-Hassan Khan, D. Zargarian, D. M. Spasyuk, New J. Chem., 2015, 39, 6649.
The Privileged Pincer-MetalPlatform: Coordination Chemistry & Applications. Topics in Organometallic Chemistry, Eds G. van Koten, R. Gossage, 2015, Vol. 54, Springer, Cham—Heidelberg—New York—Dordrecht—London, 374 pp.
J. Hao, B. Mougang-Soumé, B. Vabre, D. Zargarian, Angew. Chem., Int. Ed., 2014, 53, 3218.
J. Hao, B. Vabre, B. Mougang-Soumé, D. Zargarian, Chem. Eur. J., 2014, 20, 12544.
Organometallic Pincer Chemistry. Topics in Organometallic Chemistry, Vol. 40, Eds G. van Koten, D. Milstein, Springer, Heidelberg, 2013.
A. Castonguay, D. M. Spasyuk, N. Madern, A. L. Beauchamp, D. Zargarian, Organometallics, 2009, 28, 2134.
E. A. Gwynne, D. W. Stephan, Organometallics, 2011, 30, 4128.aaa
S. Murugesan, K. Kirchner, Dalton Trans., 2016, 45, 416.
D. M. Grove, G. van Koten, R. Zoet, J. Am. Chem. Soc., 1983, 105, 1379.
D. M. Grove, G. van Koten, P. Mul, R. Zoet, J. G. M. van der Linden, J. Legters, J. E. J. Schmitz, N. W. Murrall, A. J. Welch, Inorg. Chem., 1988, 27, 2466.
D. M. Grove, G. van Koten, W. P. Mul, A. H. van der Zeij den, J. Terheij den, Organometallics, 1986, 5, 322.
K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, G. K. Fukin, N. N. Vavilina, L. Y. Efremova, G. A. Abakumov, J. Magn. Res., 2009, 197, 36.
P. Steenwinkel, R. A. Gossage, G. van Koten, Chem. Eur. J., 1998, 4, 759.
V. Pandarus, A. Castonguay, D. Zargarian, Dalton Trans., 2008, 4756.
J. S. Fossey, C. J. Richards, J. Organomet. Chem., 2004, 689, 3056.
K. Mitsudo, T. Imura, T. Yamaguchi, H. Tanaka, Tetrahedron Lett., 2008, 49, 7287.
M. Contel, M. Stol, M. A. Casado, G. P. M. van Klink, D. D. Ellis, A. L. Spek, G. van Koten, Organometallics, 2002, 21, 4556.
K. A. Kozhanov, M. P. Bubnov, V. K. Cherkasov, G. A. Abakumov, Dokl. Chem., 2006, 407, 35.
M. Stol, D. J. M. Snelders, M. D. Godbole, R. W. A. Havenith, D. Haddleton, G. Clarkson, M. Lutz, A. L. Spek, G. P. M. van Klink, G. van Koten, Organometallics, 2007, 26, 3985.
A. Bugarin, B. T. Connell, Organometallics, 2008, 27, 4357.
D. H. Lee, J. H. Sungwon, S. Park, Bull. Korean Chem. Soc., 2008, 29, 187.
J.-P. Cloutier, B. Vabre, B. Moungang-Soumé, D. Zargarian, Organometallics, 2015, 34, 133.
J. Hurtado, A. Ibanez, R. Rojas, M. Valderrama, R. Fröhlich, J. Braz. Chem. Soc., 2011, 22.1750.
D.-D. Shao, J.-L. Niu, X.-Q. Hao, J.-F. Gong, M.-P. Song, Dalton Trans., 2011, 40, 9012.
R. Brown, J. Garcia, J. Valjus, C. Roberts, H. Tuono nen, M. Parvez, R. Roesler, Angew. Chem., Int. Ed., 2015, 54, 6274.
A. G. Nair, R. T. McBurney, M. R. D. Gatus, D. B. Walker, M. Bhadbhade, B. A. Messerle, J. Organomet. Chem., 2017, 845, 63.
S. Gu, J. Du, J. Huang, Y. Guo, L. Yang, W. Xua, W. Chen, Dalton Trans., 2017, 46, 586.
D. M. Spasyuk, D. Zargarian, A. van der Est, Organometallics, 2009, 28, 6531.
D. M. Spasyuk, D. Zargarian, Inorg. Chem., 2010, 49, 6203.
D. M. Spasyuk, S. I. Gorelsky, A. van der Est, D. Zargarian, Inorg. Chem., 2011, 50, 2661.
J. B. Smith, A. J. M. Miller, Organometallics, 2015, 34, 4669.
B.-S. Zhang, W. Wang, D.-D. Shao, X.-Q. Hao, J.-F. Gong, M.-P. Song, Organometallics, 2010, 29, 2579.
M.-J. Yang, Y.-J. Liu, J.-F. Gong, M.-P. Song, Organometallics, 2011, 30, 3793.
J.-L. Niu, Q.-T. Chen, X.-Q. Hao, Q.-X. Zhao, J.-F. Gong, M.-P. Song, Organometallics, 2010, 29, 2148.
C. A. Kruithof, H. P. Dij kstra, M. Lutz, A. L. Spek, R. J. M. K. Gebbink, G. van Koten, Organometallics, 2008, 27, 4928.
T.-a. Koizumi, T. Teratani, K. Okamoto, T. Yamamoto, Y. Shimoi, T. Kanbara, Inorg. Chim. Acta, 2010, 363, 2474.
S. M. Peterson, M. L. Helm, A. M. Appel, Dalton Trans., 2015, 44, 747.
T. Xu, M. D. Wodrich, R. Scopelliti, C. Corminboeuf, X. Hu, Proc. Natl. Acad. Sci. USA, 2017, 114, 1242.
A. Liu, X. Zhang, W. Chen, Organometallics, 2009, 28, 4868.
G. Ebeling, M. R. Meneghetti, F. Rominger, J. Dupont, Organometallics, 2002, 21, 3221.
C. S. Consorti, G. Ebeling, F. R. Flores, F. Rominger, J. Dupont, Adv. Synth. Catal., 2004, 346, 617.
A. R. Chianese, A. Mo, N. L. Lampland, R. L. Swartz, P. T. Bremer, Organometallics, 2010, 29, 3019.
U. N. Patel, D. K. Pandey, R. G. Gonnade, B. Punji, Organometallics, 2016, 35, 1785.
T. D. Franco, M. Stojanovic, S. C. Keller, R. Scopelliti, X. Hu, Helv. Chim. Acta, 2016, 99, 830.
J. Heidebrecht, C. Gendy, B. S. Gelfand, R. Roesler, Polyhedron, 2018, 143, 138.
D. A. Evers-McGregor, M. W. Bezpalko, B. M. Foxman, C. M. Thomas, Dalton Trans., 2016, 45, 1918.
H. Valdes, L. Gonzalez-Sebastian, D. Morales-Morales, J. Organomet. Chem., 2017, 845, 229.
S. N. Melnikov, K. A. Lyssenko, I. V. Ananyev, I. L. Eremenko, Russ. Chem. Bull., 2017, 66, 1550.
A. D. Ryabov, Chem. Rev., 1990, 90, 403.
M. W. Haenel, D. Jakubik, C. Krüger, P. Betz, Chem. Ber., 1991, 124, 333.
B. Vabre, Y. Canac, C. Lepetit, C. Duhayon, R. Chauvin, D. Zargarian, Chem. Eur. J., 2015, 21, 17403.
D. M. Grove, G. van Koten, H. J. C. Ubbels, R. Zoet, A. L. Spek, Organometallics, 1984, 3, 1003.
J. A. M. van Beek, G. van Koten, M. J. Ramp, N. C. Coenjaarts, D. M. Grove, K. Goublitz, M. C. Zoutberg, C. H. Stam, W. J. J. Smeets, A. L. Spek, Inorg. Chem., 1991, 30, 3059.
A. W. Kleij, R. A. Gossage, R. J. M. Klein Gebbink, N. Brinkmann, E. J. Reij erse, U. Kragl, M. Lutz, A. L. Spek, G. van Koten, J. Am. Chem. Soc., 2000, 122, 12112.
B. Vabre, F. Lindeperg, D. Zargarian, Green Chem., 2013, 15, 3188.
P. Hasche, M. Joksch, G. Vlachopoulou, H. Agarwala, A. Spa nnenberg, T. Beweries, Eur. J. Inorg. Chem., 2018, 676.
J. Dupont, N. Beydoun, M. Pfeffer, J. Chem. Soc., Dalton Trans., 1989, 1715.
P. Dani, T. Karlen, R. A. Gossage, W. J. J. Smeets, A. L. Spek, G. van Koten, J. Am. Chem. Soc., 1997, 119, 11317.
H. P. Dij kstra, M. Albrecht, S. Medici, G. P. M. van Klink, G. van Koten, Adv. Synth. Catal., 2002, 344, 1135.
M. Albrecht, P. Dani, M. Lutz, A. L. Spek, G. van Koten, J. Am. Chem. Soc., 2000, 122, 11833.
M. Asay, D. Morales-Morales, Dalton Trans., 2015, 44, 17432.
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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0385—0394, March, 2018.
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Gafurov, Z.N., Kagilev, A.A., Kantyukov, A.O. et al. Classification and synthesis of nickel pincer complexes. Russ Chem Bull 67, 385–394 (2018). https://doi.org/10.1007/s11172-018-2086-7
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DOI: https://doi.org/10.1007/s11172-018-2086-7