Backbone tuning in indenylidene–ruthenium complexes bearing an unsaturated N-heterocyclic carbene

César A. Urbina-Blanco, Xavier Bantreil, Hervé Clavier, Alexandra M. Z. Slawin and Steven P. Nolan
Beilstein J. Org. Chem. 2010, 6, 1120–1126. https://doi.org/10.3762/bjoc.6.128

Supporting Information

Detailed experimental procedures for the synthesis of complexes 5ad, 6a, 6c and 6d, and procedures for the catalysis are available in the supporting information. The CIF files of crystal structures 5ad have been deposited with the CCDC, No. 793640–793643, respectively. Copies of the data can be obtained free of charge on applications to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44 1223 336 033; http://www.ccdc.cam.ac.uk; e-mail: deposit@ccdc.cam.ac.uk.

Supporting Information File 1: Supporting Information.
Format: PDF Size: 1.1 MB Download

Cite the Following Article

Backbone tuning in indenylidene–ruthenium complexes bearing an unsaturated N-heterocyclic carbene
César A. Urbina-Blanco, Xavier Bantreil, Hervé Clavier, Alexandra M. Z. Slawin and Steven P. Nolan
Beilstein J. Org. Chem. 2010, 6, 1120–1126. https://doi.org/10.3762/bjoc.6.128

How to Cite

Urbina-Blanco, C. A.; Bantreil, X.; Clavier, H.; Slawin, A. M. Z.; Nolan, S. P. Beilstein J. Org. Chem. 2010, 6, 1120–1126. doi:10.3762/bjoc.6.128

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Escayola, S.; Bahri-Laleh, N.; Poater, A. %VBur index and steric maps: from predictive catalysis to machine learning. Chemical Society reviews 2024, 53, 853–882. doi:10.1039/d3cs00725a
  • Gorbachev, V.; Nobile, A. G.; Tsybizova, A.; Chen, P. Probing Electronic Effects in Tridentate Copper(I) Complexes by CIVP Spectroscopy. Inorganic chemistry 2023, 62, 14704–14714. doi:10.1021/acs.inorgchem.3c02065
  • Canac, Y. Carbon-Phosphorus Ligands with Extreme Donating Character. Chemical record (New York, N.Y.) 2023, 23, e202300187. doi:10.1002/tcr.202300187
  • Guillet, S. G.; Ibni Hashim, I.; Beliš, M.; Van Hecke, K.; Cazin, C. S. J.; Nolan, S. P. Mechanistic Insights into the Synthesis of [Rh(acac)(CO)(NHC)] (NHC=N‐heterocyclic carbene) Complexes Using a Weak Base. European Journal of Inorganic Chemistry 2023, 26. doi:10.1002/ejic.202300327
  • Padunnappattu, A.; Duhayon, C.; César, V.; Canac, Y. Bis(N-cyclopropenio)-imidazol-2-ylidene: An N-Heterocyclic Carbene Bearing Two N-Cationic Substituents. Organometallics 2022, 41, 2868–2878. doi:10.1021/acs.organomet.2c00429
  • Goldstein, E. L.; Ziegler, F.; Beurer, A.; Traa, Y.; Bruckner, J. R.; Buchmeiser, M. R. Cationic Molybdenum Imido Alkylidene N‐Heterocyclic Carbene Complexes Confined in Mesoporous Silica: Tuning Transition States Towards Z‐Selective Ring‐Opening Cross‐Metathesis. ChemCatChem 2022, 14. doi:10.1002/cctc.202201008
  • Shibahara, F.; Shibata, Y.; Murai, T. Imidazo[1,5-a]pyridinylidenes as π-Accepting NHC Ligands in Catalysis. Chemistry Letters 2021, 50, 1892–1900. doi:10.1246/cl.210461
  • Ziegler, F.; Kraus, H.; Benedikter, M. J.; Wang, D.; Bruckner, J. R.; Nowakowski, M.; Weißer, K.; Solodenko, H.; Schmitz, G.; Bauer, M.; Hansen, N.; Buchmeiser, M. R. Confinement Effects for Efficient Macrocyclization Reactions with Supported Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes. ACS Catalysis 2021, 11, 11570–11578. doi:10.1021/acscatal.1c03057
  • Zarate, X.; Pop, L.-C.; Treto-Suárez, M. A.; Tapia, J.; Schott, E. Structure and electronic properties of benzimidazole and cycloheptaimidazole gold N-heterocyclic carbenes. Polyhedron 2021, 205, 115259. doi:10.1016/j.poly.2021.115259
  • Popov, S.; Plenio, H. Determination of Stereoelectronic Properties of NHC Ligands via Ion Pairing and Fluorescence Spectroscopy. European Journal of Inorganic Chemistry 2021, 2021, 3708–3718. doi:10.1002/ejic.202100510
  • Hauser, P. M.; Musso, J. V.; Frey, W.; Buchmeiser, M. R. Cationic Tungsten Oxo Alkylidene N-Heterocyclic Carbene Complexes via Hydrolysis of Cationic Alkylidyne Progenitors. Organometallics 2021, 40, 927–937. doi:10.1021/acs.organomet.1c00035
  • Wei, W.; Jia, G. Comprehensive Coordination Chemistry III - Metal-Carbon Bonds of Heavier Group 7 and 8 Metals (Tc, Re, Ru, Os): Mononuclear Tc/Re/Ru/Os Complexes With Metal-Carbon Bonds. Comprehensive Coordination Chemistry III; Elsevier, 2021; pp 123–439. doi:10.1016/b978-0-08-102688-5.00049-0
  • Benedikter, M. J.; Musso, J. V.; Kesharwani, M. K.; Sterz, K. L.; Elser, I.; Ziegler, F.; Fischer, F.; Plietker, B.; Frey, W.; Kästner, J.; Winkler, M.; van Slageren, J.; Nowakowski, M.; Bauer, M.; Buchmeiser, M. R. Charge Distribution in Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes: A Combined X-ray, XAS, XES, DFT, Mössbauer, and Catalysis Approach. ACS Catalysis 2020, 10, 14810–14823. doi:10.1021/acscatal.0c03978
  • de Kock, S.; Dillen, J.; Esterhuysen, C. Steric and Electronic Effects in Gold N‐Heterocyclic Carbene Complexes Revealed by Computational Analysis. ChemistryOpen 2019, 8, 539–550. doi:10.1002/open.201900076
  • Canac, Y. Carbeniophosphines versus Phosphoniocarbenes: The Role of the Positive Charge. Chemistry, an Asian journal 2018, 13, 1872–1887. doi:10.1002/asia.201800483
  • Huynh, H. V. Electronic Properties of N-Heterocyclic Carbenes and Their Experimental Determination. Chemical reviews 2018, 118, 9457–9492. doi:10.1021/acs.chemrev.8b00067
  • Izquierdo, F.; Zinser, C. M.; Minenkov, Y.; Cordes, D. B.; Slawin, A. M. Z.; Cavallo, L.; Nahra, F.; Cazin, C. S. J.; Nolan, S. P. Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki–Miyaura Reaction. ChemCatChem 2017, 10, 601–611. doi:10.1002/cctc.201701279
  • Avinash, I.; Gupta, V.; Karthik, V.; Anantharaman, G. A straightforward synthesis of 4,5-dihalofunctionalized imidazol-2-ylidene/imidazolyl-metal complexes from trihaloimidazolium salts/imidazoles: Structure and catalytic studies. Journal of Organometallic Chemistry 2017, 851, 104–114. doi:10.1016/j.jorganchem.2017.09.018
  • Leclerc, M. C.; Da Gama, J. G.; Gabidullin, B.; Baker, R. T. A closer look at the reactivity between N-heterocyclic carbenes and fluoroalkenes. Journal of Fluorine Chemistry 2017, 203, 81–89. doi:10.1016/j.jfluchem.2017.05.012
  • Couzijn, E. P. A.; Lai, Y. Y.; Limacher, A.; Chen, P. Intuitive Quantifiers of Charge Flows in Coordinate Bonding. Organometallics 2017, 36, 3205–3214. doi:10.1021/acs.organomet.7b00365

Patents

  • GRUBBS ROBERT H; HERBERT MYLES B; WICKENS ZACHARY K; MARX VANESSA M; KEITZ BENJAMIN K; ENDO KOJI. Syntheses of Z-olefin-containing lepidopteran insect pheromones. US 8987531 B2, March 24, 2015.
  • GRUBBS ROBERT H; HERBERT MYLES B; WICKENS ZACHARY K; MARX VANESSA M. SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES. US 20130231499 A1, Sept 5, 2013.
Other Beilstein-Institut Open Science Activities