Synthesis and structure of some azolium salts
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DOI:
https://doi.org/10.15625/2525-2321.2017-00454Keywords:
N-heterocyclic carbenes, azoles, azolium saltsAbstract
The reactions between benzimidazole, imidazole, or 1,2,4-triazole with either benzyl chloride or isopropyl bromide yielded 6 azolium salts, namely 1,3-dibenzylimidazolium chloride (M1), 1,3-dibenzylbenzimidazolium chloride (M2), 1,3-dibenzyl-1,2,4-triazolium chloride (M3), 1,3-diisopropylimidazolium bromide (M4), 1,3-diisopropylbenzimidazolium bromide (M5), and 1,3-diisopropyl-1,2,4-triazolium bromide (M6). These salts can be further used as the starting compounds for the synthesis of complexes based on N-heterocyclic carbenes for various applications. The structures of M1÷M6 have been unambiguously determined by means of IR and 1H NMR spectroscopic methods.
Keywords. N-heterocyclic carbenes, azoles, azolium salts.
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References
Garrison J. C., Youngs W. J. Ag(I) N-Heterocyclic Carbene Complexes: Synthesis, Structure, and Application, Chem. Rev., 105, 4001-4005 (2005).
Herrmann W. A., Köcher C. N-Heterocyclic Carbenes, Angew. Chem. Int. Ed. Engl, 36, 2162 (1997).
Hackenberg F., Müller-Bunz H., Smith R., Streciwilk W., Zhu X., Tacke M. Novel ruthenium(II) and gold(I) NHC complexes: Synthesis, characterization, and evaluation of their anticancer properties, Organometallics, 32, 5551-5560 (2013).
Böhm V. P. W., Weskamp T., Gstöttmayr C. W. K., Herrmann W. A. Nickel-catalyzed cross-coupling of aryl chlorides with aryl grignard reagents, Angew Chem., Int. Ed., 39, 1602 (2000).
Wang X., Liu S., Jin D. X. Preparation, structure, and olefin polymerization behavior of functionalized Nickel(II) N-heterocyclic carbene complexes, Organometallics, 23, 6002 (2004).
Hahn F. E., Jahnke M. C. Heterocyclic carbenes: Synthesis and coordination chemistry, Angew. Chem., Int. Ed., 47, 3122-3172 (2008).
Crabtree R. The Organometallic chemistry of the transition metals, 4th Ed., Wiley-Interscience (2005).
Fremont de P., Marion N., Nolan S. P. Carbenes: Synthesis, properties, and organometallic chemistry, Coord. Chem. Rev., 253, 862-892 (2009).
Tran Thi Da, Nguyen Huu Dinh. Complex - Synthesis method and structural study, Vietnam Education Publishing House (2007).
