Dimetal-Binding Scaffold 2-(Pyridin-2-yl)imidazo [1,5-b]pyridazine-7-ylidene: Synthesis of Trinuclear Heterobimetallic Complexes Involving Gold-Metal Interactions.
DFT calculation
N-heterocyclic carbene
gold complex
heterobimetallic complex
metallophilic interaction
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 Sep 2023
15 Sep 2023
Historique:
received:
25
05
2023
medline:
27
6
2023
pubmed:
27
6
2023
entrez:
27
6
2023
Statut:
ppublish
Résumé
As a dimetal-binding rigid scaffold, 2-(pyridin-2-yl)imidazo[1,5-b]pyridazine-7-ylidene was introduced. The scaffold was first converted into a meridional Au,N,N-tridentate ligand through binding of a Au(I)Cl moiety at the carbene center. The Au(I) center and the N,N-chelating moiety were expected to function as metallophilic and 4e-σ-donative interaction sites, respectively, in the binding of the second metal center. In this manner, various trinuclear heterobimetallic complexes were synthesized with different 3d-metal sources, such as cationic Cu
Identifiants
pubmed: 37367483
doi: 10.1002/chem.202301673
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301673Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP20K15268
Organisme : Japan Society for the Promotion of Science
ID : JP23K13735
Organisme : Japan Society for the Promotion of Science
ID : JP21H04680
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
S. P. Nolan in N-Heterocyclic Carbenes, Wiley-VCH, 2014;
W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. 1997, 36, 2162-2187;
C. M. Crudden, D. P. Allen, Coord. Chem. Rev. 2004, 248, 2247-2273;
O. Kühl, Chem. Soc. Rev. 2007, 36, 592-607;
F. E. Hahn, M. C. Jahnke, Angew. Chem. Int. Ed. 2008, 47, 3122-3172;
L. Oehninger, R. Rubbiani, I. Ott, Dalton Trans. 2013, 42, 3269-3284;
M. H. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 2014, 510, 485-496.
N. Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776-1782;
A. Mariconda, M. Sirignano, R. Troiano, S. Russo, P. Longo, Catalysts 2022, 12, 836.
H. Amouri, Chem. Rev. 2023, 123, 230-270.
S. Nayak, S. L. Gaonkar, ChemMedChem 2021, 16, 1360-1390.
Selected examples,
V. K. Rawat, K. Higashida, M. Sawamura, ACS Catal. 2022, 12, 8325-8330;
A. Luengo, I. Marzo, V. Fernández-Moreira, M. C. Gimeno, Appl. Organomet. Chem. 2022, e6661;
Q. Teng, H. V. Huynh, Organometallics 2018, 37, 4119-4127;
M. R. D. Gatus, M. Bhadbhade, B. A. Messerle, Dalton Trans. 2017, 46, 14406-14419;
Q. Teng, H. V. Huynh, Chem. Commun. 2015, 51, 1248-1251;
B. Bertrand, A. Citta, I. L. Franken, M. Picquet, A. Folda, V. Scalcon, M. P. Rigobello, P. L. Gendre, A. Casini, E. Bodio, J. Biol. Inorg. Chem. 2015, 20, 1005-1020;
L. Boselli, M. Carraz, S. Mazères, L. Paloque, G. González, F. Benoit-Vical, A. Valentin, C. Hemmert, H. Gornitzka, Organometallics 2015, 34, 1046-1055.
M. Baradají, A. Laguna, Eur. J. Inorg. Chem. 2003, 3069-3079;
E. J. Fernández, A. Laguna, J. M. López-de-Luzuriaga, M. Monge, M. Montiel, M. E. Olmos, Inorg. Chem. 2007, 46, 2953-2955;
E. J. Fernández, A. Laguna, J. M. López-de-Luzuriaga, Dalton Trans. 2007, 1969-1981;
M. Rodríguez-Castillo, M. Monge, J. M. López-de-Luzuriaga, M. E. Olmos, A. Laguna, F. Mendizabal, Comp. Theor. Chem. 2011, 965, 163-167; Au-Au interactions have also been investigated;
H. Scbmidbaur, Gold Bull. 1990, 23, 11-21;
H. Scbmidbaur, A. Schier, Chem. Soc. Rev. 2012, 41, 370-412.
V. J. Catalano, M. A. Malwitz, A. O. Etogo, Inorg. Chem. 2004, 43, 5714-5724;
V. J. Catalano, A. O. Etogo, J. Organomet. Chem. 2005, 690, 6041-6050;
V. J. Catalano, A. L. Moore, Inorg. Chem. 2005, 44, 6558-6566;
V. J. Catalano, A. O. Etogo, Inorg. Chem. 2007, 46, 5608-5615.
V. J. Catalano, A. L. Moore, J. Shearer, J. Kim, Inorg. Chem. 2009, 48, 11362-11375;
C. E. Strasser, V. J. Catalano, Inorg. Chem. 2011, 50, 11228-11234;
M. M. Nenzel, K. Chen, V. J. Catalano, J. Coord. Chem. 2016, 69, 160-167;
B. M. Kariuki, J. A. Platts, P. D. Newman, RSC Adv. 2021, 11, 34170-34173;
V. R. Naina, F. Krätschmer, P. W. Roesky, Chem. Commun. 2022, 58, 5332-5346.
C. Kaub, S. Lebedkin, S. Bestgen, R. Köppe, M. M. Kappes, P. W. Roesky, Chem. Commun. 2017, 53, 9578-9581;
C. Kaub, S. Lebedkin, A. Li, S. V. Kruppa, P. H. Strebert, M. M. Kappes, C. Riehn, P. W. Roesky, Chem. Eur. J. 2018, 24, 6094-6104.
Other flexible pyridyl-substituted NHC scaffolds also led to locating two metals in distal positions to lose intermetallic interactions,
C. E. Strasser, V. J. Catalano, J. Am. Chem. Soc. 2010, 132, 10009-10011;
J. Wimberg, S. Meyer, S. Dechert, F. Meyer, Organometallics 2012, 31, 5025-5033;
K. Chen, M. M. Nenzel, T. M. Brown, V. J. Catalano, Inorg. Chem. 2015, 54, 6900-6909;
T. Simler, K. Müller, T. J. Feuerstein, M. T. Gamer, S. Lebedkin, M. M. Kappes, P. W. Roesky, Organometallics 2019, 38, 3649-3661.
An imidazo[5,1-a]phthalazine-2-ylidene palladium complex was reported as a related NHC-complex, whereas it was not applied to the synthesis of heterobimetallic complexes;K. G. Kishore, O. Ghashghaei, C. Estarellas, M. M. Mestre, C. Monturiol, N. Kielland, J. M. Kelly, A. F. Francisco, S. Jayawardhana, D. Muñoz-Torrero, B. Pérez, F. J. Luque, R. Gámez-Montaño, R. Lavilla, Angew. Chem. Int. Ed. 2016, 55, 8994-8998.
The reaction conditions were optimized from reported procedure; C. Liu, M. G. Yang, Z. Xiao, L. Chen, R. M. Moslin, J. S. Tokarski, D. S. Weinstein, Sulfone pyridine alkyl amide-substituted heteroaryl compounds US2019152948A1, 2019.
J. T. Hutt, Z. D. Aron, Org. Lett. 2011, 13, 5256-5259.
A. Collado, A. Gómez-Suárez, A. R. Martin, A. M. Z. Slawin, S. P. Nolan, Chem. Commun. 2013, 49, 5541-5543.
P. de Frémont, N. M. Scott, E. D. Stevens, S. P. Nolan, Organometallics 2005, 24, 2411-2418.
Deposition Numbers 2247782 (for 1), 2247783 (for 1-CuICl), 2247784 (for 1-CuI), 2247785 (for 1-CuII), 2247786 (for 1-NiII), 2247787 (for 1-CoIICl), 2247788 (for 9), and 2247789 (for 10) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Bondi van der Waals radii were applied for the calculations; A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
M. J. Calhorda, C. Ceamanos, O. Crespo, M. C. Gimeno, A. Laguna, C. Larraz, P. D. Vaz, M. D. Villacampa, Inorg. Chem. 2010, 49, 8255-8269.
V. J. Catalano, J. M. López-de-Luzuriage, M. Monge, M. E. Olmos, D. Pascual, Dalton Trans. 2014, 43, 16486-16497.
E. Hobbollahi, M. List, B. Hupp, F. Mohr, R. J. F. Berger, A. Steffen, U. Monkowius, Dalton Trans. 2017, 46, 3438-3442.
M. I. Arriortua, T. Rojo, J. M. Amigo, G. Germain, J. P. Declercq, Acta Crystallogr. 1982, B38, 1323-1324;
J. Karges, K. Xiong, O, Blacque, H. Chao, G. Gasser, Inorg. Chim. Acta. 2021, 516, 120137.
M. Barley, E. C. Constable, S. A. Corr, R. C. S. McQueen, J. C. Nutkins, M. D. Ward, M. G. B. Drew, J. Chem. Soc. Dalton Trans. 1988, 2655-2662;
C. Piguet, G. Bernardinelli, A. F. Williams, Inorg. Chem. 1989, 28, 2920-2925; A copper(I) acetonitrile complex bearing a terpyridine derivative as a N,N,N-tridentate ligand was reported, in which the four-coordinated complex adopted a highly distorted square-planar geometry;
V. Madhu, Y. Diskin-Posner, R. Neumann, Eur. J. Inorg. Chem. 2011, 1792-1796.
Bondi van der Waals radius for cobalt has not been reported. Hence, the calculated van der Waals radius (Co: 1.64 Å) was applied, in which the sum of van der Waals radii of Au and Co is estimated as 3.30 Å. The actual distances of Co-Au for 1-CoIICl were shorter than the sum of van der Waals radii;S. S. Batsanov, Inorg. Mater. 2001, 37, 871-885.
Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
R. F. W. Bader, Acc. Chem. Res. 1985, 18, 9-15;
R. F. W. Bader, Chem. Rev. 1991, 91, 893-928.
Multiwfn program ver. 3.8 for Windows was downloaded from the following website (http://sobereva.com/multiwfn/); T. Lu, F. Chen, J. Compute. Chem. 2012, 33, 580-592.
3D models were described by VMD program ver. 1.9.4a53; W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics 1996, 14, 33.
A. D. Becke, K. E. Edgecombe, J. Chem. Phys. 1990, 92, 5397-5403.
T. Lu, Q. Chen, J. Comput. Chem. 2022, 43, 539-555.
J. Österlöf, Acta Chem. Scand. 1950, 4, 374-385.
G. M. Sheldrick, Acta Crystallogr. 2015, A71, 3-8.
G. M. Sheldrick, Acta Crystallogr. 2015, C71, 3-8.
V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.