Abstract
New tertiary ferrocenyl stibines (I and III) and bismuthine (II) have been synthesized. All these compounds have been characterized by IR, MS, and NMR spectroscopy and the molecular structures of I–III have been determined by X-ray crystallography. Compounds I–III have also been studied by cyclic voltammetry (CV). Crystal structures of homoleptic stibine and bismuthine (I, II) adopt a “propeller” configuration with the three ferrocenyl groups tilted to minimize interatomic repulsion and exhibit helicoidal chirality. The structures of I and III show that both the stibines exhibit an intramolecular C−H···C interaction. The voltammograms of stibines show that E1/2 values are more positive than that of ferrocene indicating that oxidation of Fc3Sb is slightly more challenging in comparison to ferrocene. Triferrocenyl bismuthine (II) displays two redox waves with low resolution and a non-reversible process.
REFERENCES
J. Okuda, Eur. J. Inorg. Chem. 2017, 217 (2017).
P. Štěpnička, Ferrocenes: Ligands, Materials, and Biomolecules (J. Wiley, 2008).
L. X. Dai and X. L. Hou, Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications (Wiley-VCH Verlag GmbH and Co. KGaA, Republic of China, 2010).
M. Pérez, M. Fañanás-Mastral, P. H. Bos, A. Rudolph, S. R. Harutyunyan, and B. L. Feringa, Nat. Chem. 3, 377 (2011).
M. Mato, C. Pérez-Caaveiro, L. A. Sarandeses and J. Pérez Sestelo, ACS Catal. 359, 1388 (2017).
C. T. Check, K. P. Jang, C. B. Schwamb, A. S. Wong, M. H. Wang and K. A. Scheidt, Angew. Chem. Int. Ed. 54, 4264 (2015).
A. Alkan, L. Thomi, T. Gleede, and F. R. Wurm, Polym. Chem. 6, 3617 (2015).
L. Xu, Y. X. Wang, L. J. Chen, and H. B. Yang, Chem. Soc. Rev. 44, 2148 (2015).
G. Jaouen, A. Vessières, and S. Top, Chem. Soc. Rev. 44, 8802 (2015).
H. V. Nguyen, Z. Zhao, A. Sallustrau, S. L. Horswell, L. Male, A. Mulas, and J. H. R. Tucker, Chem. Commun. 48, 12165 (2012).
S. S. Braga and A. M. S. Silva, Organometallics 32, 5626 (2013).
I. Arellano, F. Rodríguez-Ramos, M. González-Andrade, A. Navarrete, M. Sharma, N. Rosas, and P. Sharma, J. Heterocycl. Chem. 53, 1147 (2016).
Y. Torubaev, P. Mathur, M. Tauqeer, M. M. Shaikh, G. K. Lahiri, A. Pasynskii, A. Pavlova, and V. J. Grinberg, Organomet. Chem. 749, 115 (2014).
J. Yan, K. Yue, X. Fan, X. Xu, J. Wang, M. Qin, Q. Zhang, X. Hou, X. Li, and Y. Wang, Eur. J. Med. Chem. 246, 115004 (2023).
K. Schlotter, F. Boeckler, H. Hübner, and P. Gmeiner, J. Med. Chem. 48, 3696 (2005).
M. Patra and G. Gasser, Nat. Rev. Chem. 1, 1 (2017).
A. Singh, I. Lumb, V. Mehra, and V. Kumar, Dalton Trans. 48, 2840 (2019).
T. López and A. Campero, J. Organomet. Chem. 378, 91 (1989).
B. Wrackmeyer, U. Dörfler, W. Milius, and M. Herberhold, Z. Naturforsch. B 50, 201 (1995).
S. A. Belova, A. S. Belov, N. N. Efimov, A. A. Pavlov, Y. V. Nelubina, V. V. Novikov, and Y. Z. Voloshin, Russ. J. Inorg. Chem. 67, 1151 (2022).
B. Bagh, N. C. Breit, K. Harms, G. Schatte, I. J. Burgess, H. Braunschweig, and J. Müller, Inorg. Chem. 51, 11155 (2012).
B. Wrackmeyer, E. V. Klimkina, T. Ackermann, and W. Milius, Inorg. Chim. Acta 362, 3941 (2009).
F. Voigt, A. Fischer, C. Pietzsch, and K. Jacob, Z. Anorg. Allg. Chem. 627, 2337 (2001).
M. J. MacLachlan, M. Ginzburg, N. Coombs, N. P. Raju, J. E. Greedan, G. A. Ozin, and I. Manners, J. Am. Chem. Soc. 122, 3878 (2000).
A. Houlton, R. M. G Roberts, and J. Silver, J. Chem. Soc. Dalton Trans. 1990, 1543 (1990).
A. Muller, G. Steyl, and A. Roodt, Acta Crystallogr. C. Cryst. Struct. Comm. 60, m386 (2000).
I. R. Butler, M. G. B. Drew, A. G. Caballero, P. Gerner, and C. H. Greenwell, J. Organomet. Chem. 679, 59 (2003).
E. Hecht, Z. Anorg. Allg. Chem. 626, 759 (2000).
M. J. Maclachlan, A. J. Lough, W. E. Geiger, and I. Manners, Organometallics 17, 1873 (1998).
C. Spang, F. T. Edelmann, M. Noltemeyer and H. W. Roesky, Chem. Ber. 122, 1247 (1989).
G. P. Sollott and W. R. Peterson, J. Org. Chem. 30, 839 (1965).
Y. V. Torubaev, I. V. Skabitsky, and A. Raghuvanshi, J. Organomet. Chem. 2021, 951 (2021).
B. Nayyar, S. Koop, M. Lutter and K. Jurkschat, Eur. J. Inorg. Chem. 2017, 3233 (2017).
V. Chandrasekhar and R. Thirumoorthi, Organometallics 26, 5415 (2007).
D. Perez, C. Herrera, M. Sharma, R. Gutierrez, S. Hernández, A. Toscano, and P. Sharma, J. Organomet. Chem. 743, 97 (2013).
E. Alcantara, P. Sharma, D. Perez, A. Cabrera, J. Vásquez, R. Gutiérrez, S. Hernández, and A. Toscano, Synth. React. Inorg. Metal-Organic Nano-Metal Chem. 42, 1139 (2012).
C. P. Villamizar C., B. Anzaldo, P. Sharma, R. Gutiérrez Pérez, F. del Río-Portilla, and A. R. Toscano, Inorg. Chim. Acta 502, 119353 (2020).
R. C. J. Atkinson, V. C. Gibson, and N. J. Long, Chem. Soc. Rev. 33, 313 (2004).
N. Kataoka, Q. Shelby, J. P. Stambuli and J. F. Hartwig, J. Org. Chem. 67, 5553 (2002).
L. G. Lavrenova, A. A. Mishchenko, I. V. Oleynik, E. V. Korotaev, A. N. Lavrov, M. A. Grebenkina, L. A. Sheludyakova, L. S. Klyushova, and I. I. Oleynik, Russ. J. Gen. Chem. 91, 2167 (2021).
V. S. Sergienko and A. V. Churakov, Russ. J. Gen. Chem. 93, 2311 (2023).
A. Tongi and T. Hayashi, Ferrocenes−Homogeneous Catalysis−Organic Synthesis−Materials Science (Weinheim VCH, Tokio, 1995, vol. 118).
F. Delgado-Pena, D. R. Talham and D. O. Cowan, J. Organomet. Chem. 253, C43 (1983).
A. E. Ermoshkin, N. P. Makarenko and K. I. Sakodynskii, J. Chromatogr. A 290, 377 (1984).
B. Anzaldo, P. Sharma, C. P. Villamizar, R. González, R. G. Pérez, and A. Rosas, Russ. J. Coord. Chem. 48, 839 (2022).
D. Pérez, P. Sharma, N. Rosas, A. Cabrera, J. L. Arias, F. del Rio-Portilla, J. Vazquez, R. Gutierrez, and A. Toscano, J. Organomet. Chem. 693, 3357 (2008).
D. Pérez, P. Sharma, A. Cabrera, N. Rosas, I. Arellano, A. Toscano, and S. Hernández, Polyhedron 28, 3115 (2009).
A. M. Ortiz, P. Sharma, D. Pérez, N. Rosas, A. Cabrera, L. Velasco, A. Toscano, and S. Hernández, J. Organomet. Chem. 694, 2037 (2009).
P. Sharma, J. G. Lopez, C. Ortega, N. Rosas, A. Cabrera, C. Alvarez, A. Toscano, and E. Reyes, Inorg. Chem. Commun. 9, 82 (2006).
Funding
This research was funded by DGAPA-UNAM (IN209020) and CONAHCYT (Fellowship 368610) for financial support.
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The supporting information includes crystallographic data, NMR spectra, IR and mass spectrometry. The CIF file containing complete information on the studied structure was deposited with CCDC nos. 226161, 1900165, 226162, and is freely available upon request from the following web site: www.ccdc.cam.ac.uk/data_request/cif.
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Rocio Rosales, Villamizar C., C.P., Dymarcus, R. et al. Homoleptic Ferrocenyl Stibine and Bismuthine: Synthesis and Characterization. Russ. J. Inorg. Chem. 68, 1963–1971 (2023). https://doi.org/10.1134/S0036023623602696
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DOI: https://doi.org/10.1134/S0036023623602696