Abstract
A new method for the synthesis of complexes PtIV(NHC)X4L (NHC is N-heterocyclic carbene of imidazole or benzimidazole series; X = Cl, Br; L is N-coordinated pyridine or NHC) based on mechanochemical oxidation of complexes PtII(NHC)X2L with dichloroiodobenzene (PhICl2) or pyridinium hydrobromide perbromide (PyHBr3) was proposed. Mechanochemical activation led to reduction in the synthesis time and increase in the selectivity of halogenation and yields of the target PtIV complexes (74–98%) as compared to the reaction in solutions.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Four Volumes, Eds B. Cornils, W. A. Herrmann, M. Beller, and R. Paciello, John Wiley & Sons, 2017, 1745 р.
J. A. Labinger, Chem. Rev., 2017, 117, 8483.
Y. Fort, C. Comoy, in N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools, The Royal Society of Chemistry, 2016, p. 375.
G. A. Abakumov, A. V. Piskunov, V. K. Cherkasov, I. L. Fedushkin, V. P. Ananikov, D. B. Eremin, E. G. Gordeev, I. P. Beletskaya, A. D. Averin, M. N. Bochkarev, A. A. Trifonov, U. M. Dzhemilev, V. A. D'yakonov, M. P. Egorov, A. N. Vereshchagin, M. A. Syroeshkin, V. V. Jouikov, A. M. Muzafarov, A. A. Anisimov, A. V. Arzumanyan, Y. N. Kononevich, M. N. Temnikov, O. G. Sinyashin, Y. H. Budnikova, A. R. Burilov, A. A. Karasik, V. F. Mironov, P. A. Storozhenko, G. I. Shcherbakova, B. A. Trofimov, S. V. Amosova, N. K. Gusarova, V. A. Potapov, V. B. Shur, V. V. Burlakov, V. S. Bogdanov, M. V. Andreev, Russ. Chem. Rev., 2018, 87, 393.
A. A. Shteinman, Russ. Chem. Bull., 2016, 65, 1930.
V. M. Chernyshev, O. V. Khazipov, M. A. Shevchenko, A. Y. Chernenko, A. V. Astakhov, D. B. Eremin, D. V. Pasyukov, A. S. Kashin, V. P. Ananikov, Chem. Sci., 2018, 9, 5564.
A. Vigalok, Acc. Chem. Res., 2015, 48, 238.
D. A. Petrone, J. Ye, M. Lautens, Chem. Rev., 2016, 116, 8003.
D. Meyer, S. Ahrens, T. Strassner, Organometallics, 2010, 29, 3392.
V. Khlebnikov, M. Heckenroth, H. Müller-Bunz, M. Alb recht, Dalton Trans., 2013, 42, 4197.
M. Bouche, G. Dahm, M. Wantz, S. Fournel, T. Achard, S. Bellemin-Laponnaz, Dalton Trans., 2016, 45, 11362.
V. N. Demidov, Yu. N. Kukushkin, L. N. Vedeneeva, A. N. Belyaev, J. Gen. Chem. USSR, 1988, 58, 652.
N. R. Rightmire, T. P. Hanusa, Dalton Trans., 2016, 45, 2352.
J. L. Howard, Q. Cao, D. L. Browne, Chem. Sci., 2018, 9, 3080.
V. V. Boldyrev, Russ. Chem. Bull., 2018, 67, 933.
J. G. Hernández, T. Friščić, Tetrahedron Lett., 2015, 56, 4253.aaaaaa
S. L. James, C. J. Adams, C. Bolm, D. Braga, P. Collier, T. Friščić, F. Grepioni, K. D. M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. G. Orpen, I. P. Parkin, W. C. Shearouse, J. W. Steed, D. C. Waddell, Chem. Soc. Rev, 2012, 41, 413.
M. Leonardi, M. Villacampa, J. C. Menéndez, Chem. Sci., 2018, 9, 2042.
N. Z. Lyakhov, T. F. Grigorieva, A. P. Barinova, I. A. Vorsina, Russ. Chem. Rev., 2010, 79, 189.
J. D. Egbert, A. M. Z. Slawin, S. P. Nolan, Organometallics, 2013, 32, 2271.
C. J. Adams, M. Lusi, E. M. Mutambi, A. Guy Orpen, Chem. Commun., 2015, 51, 9632.
A. Beillard, E. Golliard, V. Gillet, X. Bantreil, T.-X. Métro, J. Martinez, F. Lamaty, Chem. Eur. J., 2015, 21, 17614.
A. Beillard, X. Bantreil, T.-X. Métro, J. Martinez, F. Lamaty, Dalton Trans., 2016, 45, 17859.
A. Beillard, X. Bantreil, T.-X. Metro, J. Martinez, F. Lamaty, New J. Chem., 2017, 41, 1057.
C. J. Adams, M. Lusi, E. M. Mutambi, A. G. Orpen, Cryst. Growth Des., 2017, 17, 3151.
A. Beillard, T.-X. Métro, X. Bantreil, J. Martinez, F. Lamaty, Chem. Sci., 2017, 8, 1086.
O. V. Khazipov, M. A. Shevchenko, A. Y. Chernenko, A. V. Astakhov, D. V. Pasyukov, D. B. Eremin, Y. V. Zubavichus, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2018, 37, 1483.
J. A. Davies, C. M. Hockensmith, V. Y. Kukushkin, Y. N. Kukushkin, in Synthetic Coordination Chemistry: Principles and Practice, World Scientific, Singapore, 1996, p. 222.
C. Djerassi, C. R. Scholz, J. Am. Chem. Soc., 1948, 70, 417.
M. V. Raman, N. S. Ravichandran, J. Indian Chem. Soc., 2005, 82, 443.
E. Lee, J. Lee, D. V. Yandulov, Eur. J. Inorg. Chem., 2017, 2017, 2058.
A. K. Banerjee, M. S. Laya, W. J. Vera, Russ. Chem. Rev., 2001, 70, 971.
Y. A. Titova, O. V. Fedorova, G. L. Rusinov, V. N. Charushin, Russ. Chem. Rev., 2015, 84, 1294.
L. Andre, in Modern Solvents in Organic Synthesis. Topics in Current Chemistry, Ed. P. Knochel, Springer, Berlin, Heidelberg, 1999, vol. 206, p. 153.
V. A. Basiuk, Russ. Chem. Rev., 1995, 64, 1003.
Y. Han, H. V. Huynh, G. K. Tan, Organometallics, 2007, 26, 4612.
A. V. Astakhov, O. V. Khazipov, E. S. Degtyareva, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2015, 34, 5759.
A. V. Astakhov, O. V. Khazipov, A. Y. Chernenko, D. V. Pasyukov, A. S. Kashin, E. G. Gordeev, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2017, 36, 1981.
M. Bouché, G. Dahm, A. Maisse-François, T. Achard, S. Bellemin-Laponnaz, Eur. J. Inorg. Chem., 2016, 2016, 2828.
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv., 2008, 64, 112.
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2003–2009, November, 2018.
Rights and permissions
About this article
Cite this article
Chikunov, I.E., Ranny, G.S., Astakhov, A.V. et al. Mechanochemical synthesis of platinum(IV) complexes with N-heterocyclic carbenes. Russ Chem Bull 67, 2003–2009 (2018). https://doi.org/10.1007/s11172-018-2321-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2321-2