Abstract
New binuclear MnPt µ-vinylidene complexes Cp(CO)2Mn(µ-C=CHPh)Pt(CN–Ad)(L) [L=PPh3 (1a), P(OPri)3 (2a)] bearing a terminal platinum-coordinated 1-adamantyl isocyanide ligand were prepared by the treatment of Cp(CO)2Mn(µ-C=CHPh)Pt(CO)(L) [L=PPh3 (1b), P(OPri)3 (2b)] with CN-Ad. At the same time the reaction between Cp(CO)2Mn(µ-C=CHPh)Pt(L)2 [L=PPh3 (1c), P(OPri)3 (2c)] and CN-Ad did not proceed. The new complexes were characterized by IR and 1H, 13C, 31P NMR spectroscopy. The molecular structure of Cp(CO)2Mn(µ-C=CHPh)Pt(CN–Ad)[P(OPri)3] (2a) was determined by an X-ray diffraction study. The redox properties of the new complexes and their reactions of chemical oxidation were studied. An influence of the platinum-coordinated 1-adamantyl isocyanide ligand on the properties of the synthesized µ-vinylidene compounds 1a and 2a was revealed.
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Notes
The application of different working electrodes offers an opportunity to study the oxidation and reduction properties of compounds in the wide range of accessible potentials. The measurement region of potentials in acetonitrile (vs. Ag/0.1 M AgNO3 in MeCN) is from 0.30 to − 3.20 V at DME, from 2.00 to − 2.00 V, and from 2.00 to − 2.50 V at the Pt and GC electrodes, respectively.
References
Giustiniano M, Basso A, Mercalli V et al (2017) To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis. Chem Soc Rev 46:1295–1357. https://doi.org/10.1039/C6CS00444J
Altundas B, Marrazzo J-PR, Fleming FF (2020) Metalated isocyanides: formation, structure, and reactivity. Org Biomol Chem 18:6467–6482. https://doi.org/10.1039/D0OB01340D
Lygin AV, de Meijere A (2010) Isocyanides in the synthesis of nitrogen heterocycles. Angew Chem Int Ed 49:9094–9124. https://doi.org/10.1002/anie.201000723
Boyarskiy VP, Bokach NA, Luzyanin KV, Kukushkin VY (2015) Metal-mediated and metal-catalyzed reactions of isocyanides. Chem Rev 115:2698–2779. https://doi.org/10.1021/cr500380d
Collet JW, Roose TR, Ruijter E et al (2020) Base metal catalyzed isocyanide insertions. Angew Chem Int Ed 59:540–558. https://doi.org/10.1002/anie.201905838
Knorn M, Lutsker E, Reiser O (2020) Isonitriles as supporting and non-innocent ligands in metal catalysis. Chem Soc Rev 49:7730–7752. https://doi.org/10.1039/d0cs00223b
Sutton GD, Olumba ME, Nguyen YH, Teets TS (2021) The diverse functions of isocyanides in phosphorescent metal complexes. Dalton Trans 50:17851–17863. https://doi.org/10.1039/d1dt03312c
Angelici RJ, Lazar M (2008) Isocyanide ligands adsorbed on metal surfaces: Applications in catalysis, nanochemistry, and molecular electronics. Inorg Chem 47:9155–9165. https://doi.org/10.1021/ic800513t
Massarotti A, Brunelli F, Aprile S et al (2021) Medicinal chemistry of isocyanides. Chem Rev 121:10742–10788. https://doi.org/10.1021/acs.chemrev.1c00143
Galli U, Tron GC, Purghè B et al (2020) Metabolic fate of the isocyanide moiety: are isocyanides pharmacophore groups neglected by medicinal chemists? Chem Res Toxicol 33:955–966. https://doi.org/10.1021/acs.chemrestox.9b00504
Zhang X, Evanno L, Poupon E (2020) Biosynthetic routes to natural isocyanides. Eur J Org Chem 2020:1919–1929. https://doi.org/10.1002/ejoc.201901694
Michelin RA, Pombeiro AJL, Guedes da Silva MFC (2001) Aminocarbene complexes derived from nucleophilic addition to isocyanide ligands. Coord Chem Rev 218:75–112. https://doi.org/10.1016/S0010-8545(01)00358-7
Joshi KK, Mills OS, Pauson PL et al (1965) An iron complex with a bridging isonitrile group. Chem Commun I:181–182. https://doi.org/10.1039/c19650000181
Adams RD, Cotton FA, Troup JM (1974) Low-valent metal isocyanine complexes. V. Structure and dynamical stereochemistry of bis(pentahaptocyclopentadienyl)tricarbonyl(tert-butyl isocyanide)diiron(Fe-Fe),(η5-C5H5)2F22(CO)3[CNC(CH3)3]. Inorg Chem 13:257–262. https://doi.org/10.1021/ic50132a003
Marchetti F (2018) Constructing organometallic architectures from aminoalkylidyne diiron complexes. Eur J Inorg Chem 2018:3987–4003. https://doi.org/10.1002/ejic.201800659
Marchetti F, Zacchini S, Zanotti V (2015) C-N coupling of isocyanide ligands promoted by acetylide addition to diiron aminocarbyne complexes. Organometallics 34:3658–3664. https://doi.org/10.1021/acs.organomet.5b00515
Arrigoni F, Bertini L, De Gioia L et al (2017) Mechanistic insight into electrocatalytic H2 production by [Fe2(CN){μ-CN(Me)2}(μ-CO)(CO)(Cp)2]: effects of dithiolate replacement in [FeFe] hydrogenase models. Inorg Chem 56:13852–13864. https://doi.org/10.1021/acs.inorgchem.7b01954
Arrigoni F, Bertini L, De Gioia L et al (2020) On the importance of cyanide in diiron bridging carbyne complexes, unconventional [FeFe]-hydrogenase mimics without dithiolate: an electrochemical and DFT investigation. Inorg Chim Acta 510:119745. https://doi.org/10.1016/j.ica.2020.119745
Knorr M, Strohmann C (1998) Synthesis, reactivity, and molecular structures of bis(diphenylphosphanyl)amine- and bis(diphenylphosphanyl)amide-bridged heterobimetallic μ-isonitrile- and μ-aminocarbyne complexes (Fe−Pt). Eur J Inorg Chem 1998:495–499. https://doi.org/10.1002/(SICI)1099-0682(199804)1998:4%3c495::AID-EJIC495%3e3.0.CO;2-U
Knorr M, Strohmann C (1999) Syntheses, structures, and reactivity of dinuclear Molybdenum−Platinum and Tungsten−Platinum complexes with bridging carbonyl, sulfur dioxide, isonitrile, and aminocarbyne ligands and a dppa backbone (dppa = Ph2PNHPPh2). Organometallics 18:248–257. https://doi.org/10.1021/om980756v
Knorr M, Strohmann C (2000) Reactivity of silyl-substituted heterobimetallic Iron-Platinum hydride complexes towards unsaturated molecules, I alkyne insertions into the Platinum-hydride bond, phosphane-induced σ-alkenyl – µ-vinylidene rearrangements and formation of µ-isonitrile. Eur J Inorg Chem. https://doi.org/10.1002/(SICI)1099-0682(200002)2000:2%3c241::AID-EJIC241%3e3.0.CO;2-Y
Braunstein P, Knorr M, Stährfeldt T (1994) Heterobimetallic templates for Carbon-Carbon bond formation by migratory insertion reactions involving CO, isonitriles or olefins. J Chem Soc, Chem Commun 14:1913–1914. https://doi.org/10.1039/C39940001913
Knorr M, Jourdain I, Mohamed AS et al (2015) Synthesis and reactivity of bis(diphenylphosphino)amine-bridged heterobimetallic Iron-Platinum μ-isonitrile and μ-aminocarbyne complexes. J Organomet Chem 780:70–85. https://doi.org/10.1016/j.jorganchem.2014.12.028
Chudin OS, Verpekin VV, Kondrasenko AA et al (2020) The new μ-phenylvinylidene RePt complexes containing Platinum-bound 1-(isocyanomethylsulfonyl)- 4-methylbenzene. J Sib Fed Univ Chem 13:489–498. https://doi.org/10.17516/1998-2836-0200
Kalinin VN, Derunov VV, Lusenkova MA et al (1989) Reactions of vinylidene and allenylidene cymantrene derivatives with isonitriles. J Organomet Chem 379:303–309. https://doi.org/10.1016/0022-328X(89)85170-8
Antonova AB, Kovalenko SV, Petrovsky ED et al (1985) Chemistry of vinylidene complexes. III. Binuclear manganese-platinum complexes with bridging phenylvinylidene ligand. Inorg Chim Acta 96:1–7. https://doi.org/10.1016/S0020-1693(00)93729-0
Antonova AB, Kovalenko SV, Korniyets ED et al (1985) Chemistry of vinylidene complexes. V. The ligand substitution reactions at the platinum atom in complexes Cp(CO)2MnPt(µ-C=CHPh)L2. Inorg Chim Acta 105:153–163. https://doi.org/10.1016/S0020-1693(00)90555-3
Antonova AB, Kovalenko SV, Johansson AA et al (1991) Chemistry of vinylidene complexes X. Synthesis and characterization of the vinylidene bridged complexes Cp(CO)2MnPt(μ-C=CHPh)(P-P) with chelating diphosphine ligands P-P = dppm, dppe or dppp at the platinum atom. Inorg Chim Acta 182:49–54. https://doi.org/10.1016/S0020-1693(00)85185-3
Johansson AA, Antonova AB, Pavlenko NI, Rubaylo AI (1997) Infrared study of transformation of a terminal carbonyl ligand into a bridging one in the MnPt and MnPd μ-vinylidene complexes. J Mol Struct 408–409:329–332. https://doi.org/10.1016/S0022-2860(96)09541-5
Antonova AB, Verpekin VV, Chudin OS et al (2013) Chemistry of vinylidene complexes. XXI. Synthesis, spectroscopic and structural study of the RePt and MnPt μ–vinylidene complexes. Inorg Chim Acta 394:328–336. https://doi.org/10.1016/j.ica.2012.06.038
Chudin OS, Verpekin VV, Kondrasenko AA et al (2020) Chemistry of vinylidene complexes. XXV. Synthesis and reactions of binuclear µ-vinylidene RePt complexes containing phosphite ligands. Spectroscopic, structural and electrochemical study. Inorg Chim Acta 505:119463. https://doi.org/10.1016/j.ica.2020.119463
Cordero B, Gómez V, Platero-Prats AE et al (2008) Covalent radii revisited. Dalton Trans. https://doi.org/10.1039/b801115j
Vasiliev AD, Antonova AB, Chudin OS (2007) μ-Carbonyl-1:2κ 2 C -carbonyl-1κ C -(1 η5-cyclopentadienyl)(μ-phenylvinylidene)bis(triphenylphosphine-2κ P )manganeseplatinum( Mn—Pt). Acta Crystallogr Sect E Struct Reports Online 63:m2097–m2097. https://doi.org/10.1107/S1600536807032254
Li M, Liska T, Swetz A et al (2020) (Isonitrile)platinum(II) complexes of an amido bis(N-heterocyclic carbene) pincer ligand. Organometallics 39:1667–1671. https://doi.org/10.1021/acs.organomet.0c00065
Obanda A, Martinez K, Schmehl RH et al (2017) Expanding the scope of ligand substitution from [M(S2C2Ph2] (M = Ni2+, Pd2+, Pt2+) to afford new heteroleptic dithiolene complexes. Inorg Chem 56:10257–10267. https://doi.org/10.1021/acs.inorgchem.7b00971
Obanda A, Valerius K, Mague JT et al (2020) Group 10 metal dithiolene bis(isonitrile) complexes: synthesis, structures, properties, and reactivity. Organometallics 39:2854–2870. https://doi.org/10.1021/acs.organomet.0c00375
Burmakina GV, Verpekin VV, Zimonin DV et al (2018) Effect of ligands coordinated at Platinum atom on redox properties of binuclear Manganese-Platinum phenylvinylidene complexes. J Sib Fed Univ Chem 11:543–551
Novikova LN, Peterleitner MG, Sevumyan KA et al (2001) Oxidative dehydrodimerization of manganese phenylvinylidene complex (η5-C5H5)(CO)2Mn=C=C(H)Ph. X-ray structure of phenyl(trityl)vinylidene complex (η5-C5H5)(CO)2Mn=C=C(CPh3)Ph. J Organomet Chem 631:47–53. https://doi.org/10.1016/S0022-328X(01)01030-0
Burmakina GV, Verpekin VV, Chudin OS et al (2013) Electrochemical study of new binuclear heterometallic vinylidene complexes with the Re-Pt Bond. J Sib Fed Univ Chem 1:51–59
Verpekin VV, Vasiliev AD, Kondrasenko AA et al (2018) Chemistry of vinylidene complexes. XXIV. A new μ-vinylidene complex containing RePt core, and platinum-bound carbonyl ligand. Spectroscopic, structural and electrochemical study. J Mol Struct 1163:308–315. https://doi.org/10.1016/j.molstruc.2018.03.020
Sasaki T, Eguchi S, Katada T (1974) Synthesis of adamantane derivatives. XXV. Synthesis and reactions of 1- and 2-adamantyl isocyanides. J Org Chem 39:1239–1242. https://doi.org/10.1021/jo00923a017
Connelly NG, Geiger WE (1996) Chemical redox agents for organometallic chemistry. Chem Rev 96:877–910
Krause L, Herbst-Irmer R, Sheldrick GM, Stalke D (2015) Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. J Appl Crystallogr 48:3–10. https://doi.org/10.1107/S1600576714022985
Sheldrick G. M. (2012) TWINABS–Bruker AXS scaling for twinned crystals
Sheldrick GM (2015) SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr Sect A Found Adv 71:3–8. https://doi.org/10.1107/S2053273314026370
Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Crystallogr Sect C Struct Chem 71:3–8. https://doi.org/10.1107/S2053229614024218
Acknowledgements
Physical-chemical characteristics were obtained in the Krasnoyarsk Regional Centre of Research Equipment, Siberian Branch of the Russian Academy of Sciences.
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This work was conducted within the framework of the budget project 0287–2021-0012 for Institute of Chemistry and Chemical Technology SB RAS.
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V.V. analyzed and summarized row data, wrote and edited the main manuscript text. O.Ch. synthesized initial compounds, performed reactions and isolation of products, prepared samples for NMR spectroscopy, grown crystals for X-ray diffraction study. A.K. performed NMR experiments, NMR data curation. G.B. wrote the draft of electrochemical part of the manuscript, edited the main manuscript text, electrochemical data curation. A.V. performed X-ray crystallography experiment, X-ray data curation, prepared Fig. 1. D.Z. performed electrochemical experiments, prepared Fig. 2. A.R. project administration, funding acquisition. All authors reviewed the manuscript.
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Verpekin, V.V., Chudin, O.S., Kondrasenko, A.A. et al. Chemistry of vinylidene complexes—XXVII—new µ-vinylidene MnPt complexes with platinum-coordinated 1-adamantyl isocyanide ligand: spectroscopic, structural and electrochemical study. Transit Met Chem 47, 283–292 (2022). https://doi.org/10.1007/s11243-022-00511-w
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DOI: https://doi.org/10.1007/s11243-022-00511-w