Abstract
New complex compounds[(2-clpy)2Pd(OOCMe)2] (I), [{(Ph)Pd(2-clpy)}2(OOCMe)4Pd]·3C6H6 (II), and [{(Ph)Pd(2-clpy)}2(OOCMe)4Pd] (III) are obtained in the interaction of palladium acetate [Pd3(OOCMe)6] with 2-chloropyridine (2-clpy) and structurally characterized by single crystal X-ray diffraction. It is found that in the inert medium, mononuclear compound I forms and it can be isolated in the crystalline state, while trinuclear complexes II and III are the products of benzene metalation with palladium under mild conditions.
REFERENCES
X.-F. Wu, P. Anbarasan, H. Neumann, and M. Beller. From noble metal to Nobel Prize: palladium-catalyzed coupling reactions as key methods in organic synthesis. Angew. Chem., Int. Ed., 2010, 49, 9047-9050. https://doi.org/10.1002/anie.201006374
L. S. Hegedus, G. F. Allen, and D. J. Olsen. Palladium-assisted cyclization-insertion reactions. Synthesis of functionalized heterocycles. J. Am. Chem. Soc., 1980, 102, 3583-3587. https://doi.org/10.1021/ja00530a044
N. Kaur, Y. Verma, P. Grewal, N. Ahlawat, P. Bhardwaj, and N. K. Jangid. Palladium acetate assisted synthesis of five-membered N-polyheterocycles. Synth. Commun., 2020, 50, 1567-1621. https://doi.org/10.1080/00397911.2020.1723640
R. F. Heck and J. P. Nolley Jr. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem., 1972, 37, 2320-2322. https://doi.org/10.1021/jo00979a024
K. S. M. Salih and Y. Baqi. Microwave-assisted palladium-catalyzed cross-coupling reactions: generation of carbon-carbon bond. Catalysts, 2020, 10, 4. https://doi.org/10.3390/catal10010004
P.-E. Broutin, I. Čerňa, M. Campaniello, F. Leroux, and F. Colobert. Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki–Miyaura biphenyl synthesis. Org. Lett., 2004, 6, 4419-4422. https://doi.org/10.1021/ol048303b.
W. A. Carole and T. J. Colacot. Understanding palladium acetate from a user perspective. Chem. Eur. J., 2016, 22, 7686-7695. https://doi.org/10.1002/chem.201601450
S. M. Ghodse and V. N. Telvekar. Synthesis of 2-phenyl pyridine derivatives from aryl ketones and 1,3-diaminopropane using palladium acetate as a catalyst. Tetrahedron Lett., 2017, 58, 524-526. https://doi.org/10.1016/j.tetlet.2016.12.075
R. J. Pakula, M. Srebro-Hooper, C. G. Fry, H. J. Reich, J. Autschbach, and J. F. Berry. Palladium acetate revisited: Unusual ring-current effects, one-electron reduction, and metal–metal bonding. Inorg. Chem., 2018, 57, 8046-8049. https://doi.org/10.1021/acs.inorgchem.8b01369
S. B. Halligudi, K. N. Bhatt, N. H. Khan, R. I. Kurashy, and K. Venkatsubramanian. Synthesis, structural characterization and catalytic carbonylation of nitrobenzene and amines by mononuclear palladium(II) complexes containing substituted pyridine ligands. Polyhedron, 1996, 15, 2093-2101. https://doi.org/10.1016/0277-5387(95)00470-X
I. Kamiya, E. Nishinaka, and A. Ogawa. Palladium(II) acetate in pyridine as an effective catalyst for highly regioselective hydroselenation of alkynes. J. Org. Chem., 2005, 70, 696-698. https://doi.org/10.1021/jo048727j
K. M. Engle and J.-Q. Yu. Developing ligands for palladium(II)-catalyzed C–H functionalization: Intimate dialogue between ligand and substrate. J. Org. Chem., 2013, 78, 8927-8955. https://doi.org/10.1021/jo400159y
A. Krogul, J. Skupińska, and G. Litwinienko. Tuning of the catalytic properties of PdCl2(XnPy)2 complexes by variation of the basicity of aromatic ligands. J. Mol. Catal. A: Chem., 2014, 385, 141-148. https://doi.org/10.1016/j.molcata.2014.01.020
C. A. Salazar, J. J. Gair, K. N. Flesch, I. A. Guzei, J. C. Lewis, and S. S. Stahl. Catalytic behavior of mono-N-protected amino-acid ligands in ligand-accelerated C–H activation by palladium(II). Angew. Chem., Int. Ed., 2020, 59, 10873-10877. https://doi.org/10.1002/anie.202002484
G. Kurpik, A. Walczak, M. Gołdyn, J. Harrowfield, and A. R. Stefankiewicz. Pd(II) complexes with pyridine ligands: substituent effects on the NMR data, crystal structures, and catalytic activity. Inorg. Chem., 2022, 61, 14019-14029. https://doi.org/10.1021/acs.inorgchem.2c01996
D. D. Perrin and W. L. F. Armarego. Purification of Laboratory Chemicals. Oxford: Pergamon, 1988.
T. A. Stephenson, S. M. Morehouse, A. R. Powell, J. P. Heffer, and G. Wilkinson. 667. Carboxylates of palladium, platinum, and rhodium, and their adducts. J. Chem. Soc., 1965, 3632-3640. https://doi.org/10.1039/JR9650003632
R. D. Svetogorov, P. V. Dorovatovskii, and V. A. Lazarenko. Belok/XSA diffraction beamline for studying crystalline samples at Kurchatov synchrotron radiation source. Cryst. Res. Technol., 2020, 55, 1900184. https://doi.org/10.1002/crat.201900184
W. Kabsch. XDS. Acta Crystallogr., Sect. D: Biol. Crystallogr., 2010, 66(2), 125-132. https://doi.org/10.1107/s0907444909047337
APEX3, SAINT and SADABS. Madison, Wisconsin, USA: Bruker AXS, 2016.
L. Krause, R. Herbst-Irmer, G. M. Sheldrick, and D. Stalke. Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. J. Appl. Crystallogr., 2015, 48, 3-10. https://doi.org/10.1107/S1600576714022985
G. M. Sheldrick. SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3-8. https://doi.org/10.1107/S2053273314026370
G. M. Sheldrick. Crystal structure refinement with SHELXL. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3-8. https://doi.org/10.1107/S2053229614024218
O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann. OLEX2: A complete structure solution, refinement and analysis program. J. Appl. Crystallogr., 2009, 42, 339-341. https://doi.org/10.1107/S0021889808042726
S. V. Kravtsova, I. P. Romm, A.I. Stash, and V. K. Belsky. Bis(acetato-O)bis(pyridine-N)palladium(II) monohydrate and bis(acetato-O)bis(diethylamine-N)palladium(II). Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1996, 52(9), 2201-2204. https://doi.org/10.1107/s0108270196005732
B. Milani, E. Alessio, G. Mestroni, A. Sommazzi, F. Garbassi, E. Zangrando, N. Bresciani-Pahor, and L. Randaccio. Synthesis and characterization of monochelated carboxylatopalladium(II) complexes with nitrogen-donor chelating ligands. Crystal structures of diacetato(1,10-phenanthroline)- and diacetato(2,9-dimethyl-1,10-phenanthroline)-palladium(II). J. Chem. Soc., Dalton Trans., 1994, 1903-1911. https://doi.org/10.1039/DT9940001903
I. A. Yakushev, I. A. Stebletsova, N. V. Cherkashina, A. B. Kornev, N. S. Smirnova, and A. A. Balakina. Synthesis and structural characterization of palladium(II) diacetato-(5-nitro-1,10-phenanthroline). J. Struct. Chem., 2021, 62(9), 1411-1415. https://doi.org/10.1134/S0022476621090092
A. Bondi. Van der Waals volumes and radii. J. Phys. Chem., 1964, 68, 441-451. https://doi.org/10.1021/j100785a001
M. Mantina, A. C. Chamberlin, R. Valero, C. J. Cramer, and D. G. Truhlar. Consistent van der Waals radii for the whole main group. J. Phys. Chem. A, 2009, 113, 5806-5812. https://doi.org/10.1021/jp8111556
S. A. Adonin, M. A. Bondarenko, A. S. Novikov, and M. N. Sokolov. Halogen bonding in isostructural Co(II) complexes with 2-halopyridines. Crystals, 2020, 10, 289. https://doi.org/10.3390/cryst10040289
I. J. S. Fairlamb. Redox-active NOx ligands in palladium-mediated processes. Angew. Chem., Int. Ed., 2015, 54, 10415-10427. https://doi.org/10.1002/anie.201411487
N. V. Cherkashina, A. V. Churakov, I. A. Yakushev, I. P. Stolyarov, V. N. Khrustalev, E. V. Khramov, A. A. Markov, N. S. Smirnova, Ya. V. Zubavichus, P. V. Dorovatovskii, Zh. V. Dobrokhotova, A. B. Ilyukhin, and M. N. Vargaftik. The first heterometallic acetate-bridged Pt(II)–Pd(II) complex: Synthesis, structure, and formation of bimetallic PtPd2 nanoparticles. Russ. J. Coord. Chem., 2019, 45, 253-265. https://doi.org/10.1134/S107032841904002X
N. Yu. Kozitsyna, S. E. Nefedov, A. P. Klyagina, A. A. Markov, Z. V. Dobrokhotova, Y. A. Velikodny, D. I. Kochubey, T. S. Zyubina, A. E. Gekhman, M. N. Vargaftik, and I. I. Moiseev. Novel heterometallic palladium–silver complex. Inorg. Chim. Acta, 2011, 370, 382-387. https://doi.org/10.1016/j.ica.2011.02.003
I. A. Yakushev, M. A. Dyuzheva, N. V. Cherkashina, A. B. Kornev, N. S. Smirnova, and M. N. Vargaftik. Synthesis and crystal structure of pentanuclear heterometallic Pd(II)–La(III) acetate complex. J. Struct. Chem., 2021, 62, 1511-1515. https://doi.org/10.1134/S0022476621100048
L. Yu. Ukhin, N. A. Dolgopolova, L. G. Kuzmina, and Yu. T. Struchkov. Formation of trinuclear complexes with bisacyl--allyl ligands from palladium acetate and pyrylium salts. J. Organomet. Chem., 1981, 210, 263-272. https://doi.org/10.1016/S0022-328X(00)82238-X
T. A. Stromnova, M. V. Dayneko, A. V. Churakov, L. G. Kuzmina, J. Cámpora, P. Palma, and E. Carmona. Trinuclear palladium complexes containing terminal nitrosyl ligands: Behavior in solid state and in solution. X-ray structures of Pd3(NO)2(-OCOCX3)4(2-ArH)2 (X = F, Cl; ArH = toluene or benzene). Inorg. Chim. Acta, 2006, 359, 1613-1618. https://doi.org/10.1016/j.ica.2005.11.037
Z. M. Png, J. R. Cabrera-Pardo, J. Peiró Cadahía, and M. J. Gaunt. Diastereoselective C–H carbonylative annulation of aliphatic amines: A rapid route to functionalized -lactams. Chem. Sci., 2018, 9, 7628-7633. https://doi.org/10.1039/C8SC02855A
Funding
The work was supported by the Ministry of Science of the Russian Federation within the State Assignment for the Institute of General and Inorganic Chemistry, Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interests.
Additional information
Russian Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 3, 107273.https://doi.org/10.26902/JSC_id107273
Rights and permissions
About this article
Cite this article
Yakushev, I.A., Ogarkova, N.K., Sosunov, E.A. et al. Synthesis and Structures of Mono- and Trinuclear Complexes of Palladium(II) with 2-Chloropyridine. J Struct Chem 64, 377–385 (2023). https://doi.org/10.1134/S0022476623030046
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476623030046