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Pure Appl. Chem., 2002, Vol. 74, No. 8, pp. 1317-1325

Fischer carbene complexes. A new tool for heterocyclic synthesis

José Barluenga

Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, 33071 Oviedo, Spain

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  • Mazzoni Rita, Salmi Mauro, Zacchini Stefano, Busetto Luigi, Zanotti Valerio: Polysubstituted ferrocenes from [3 + 2] cycloaddition of alkynes with diiron bridging C3 ligands: Vinyliminium, bis-alkylidene and enimine. Journal of Organometallic Chemistry 2014, 751, 336. <>
  • Alizadeh Abdolali, Reza Esmaili zand Hamid, Saberi Vahid, Mokhtari Javad: Synthesis of 5-Aryl-3-(methylsulfanyl)-1H -pyrazoles via Three-Component Reaction of 1,1-Bis(methylsulfanyl)-2-nitroethene, Aromatic Aldehydes, and Hydrazine. HCA 2013, 96, 2240. <>
  • Barluenga José, Álvarez-Fernández Ana, Suárez-Rodríguez Tatiana, Suárez-Sobrino Ángel L., Tomás Miguel: A Simple Metal-Promoted Three-Step Access to n/5/m Angular Carbocyclic Systems. Org. Lett. 2013, 15, 488. <>
  • Suero Marcos G., De la Campa Raquel, Torre-Fernández Laura, García-Granda Santiago, Flórez Josefa: Enantioselective Multicomponent Synthesis of Fused 6-5 Bicyclic 2-Butenolides by a Cascade Heterobicyclisation Process. Chem. Eur. J. 2012, 18, 7287. <>
  • Busetto Luigi, Mazzoni Rita, Salmi Mauro, Zacchini Stefano, Zanotti Valerio: Ferrocenes Containing a Pendant Propargylic Chain Obtained via Addition of Propargyl Alcohol to μ-Vinyliminium Ligands in Diiron Complexes. Organomettalics 2012, 31, 2667. <>
  • Busetto Luigi, Marchetti Fabio, Zacchini Stefano, Zanotti Valerio: Addition of alkynes at bridging vinyliminium ligands in diiron complexes: Unprecedented diene formation by enyne-like metathesis. J Organomet Chem 2011, 696, 4051. <>
  • Nandi Bappaditya, Sinha Surajit: Alkylation of acylmetalates with alkyl halides to prepare Fischer carbene complexes: an improved protocol. Tetrahedron 2011, 67, 106. <>
  • Jin Weiwei, Yu Haifeng, Yu Zhengkun: Regioselective synthesis of multisubstituted pyrazoles via cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines. Tet Letts 2011, 52, 5884. <>
  • Helten Holger, Beckmann Manuela, Schnakenburg Gregor, Streubel Rainer: Synthesis and Reactivity of an Unusual Ferrocenophane Bis(carbene complex). Euro J Inorg Chem 2010, 2010, 2337. <>
  • Busetto Luigi, Maitlis Peter M., Zanotti Valerio: Bridging vinylalkylidene transition metal complexes. Coord Chem Rev - 2010, 254, 470. <>
  • Busetto Luigi, Marchetti Fabio, Mazzoni Rita, Salmi Mauro, Zacchini Stefano, Zanotti Valerio: [3+2+1] cycloaddition involving alkynes, CO and bridging vinyliminium ligands in diiron complexes: a dinuclear version of the Dötz reaction?. Chem Commun 2010, 46, 3327. <>
  • Strasser Christoph E., Cronje Stephanie, Raubenheimer Helgard G.: Fischer-type tungsten acyl (carbeniate), carbene and carbyne complexes bearing C5-attached thiazolyl substituents: interaction with gold(i) fragments. New J Chem 2010, 34, 458. <>
  • Fernández-Rodríguez Manuel Ángel, García-García Patricia, Aguilar Enrique: Multi-component reactions involving group 6 Fischer carbene complexes: a source of inspiration for future catalytic transformations. Chem Commun 2010, 46, 7670. <>
  • Zanotti Valerio: Reactions of bridging C3 ligands in diiron complexes: Unconventional routes to new functionalized organic frames. Pure and App Chemis 2010, 1. <>
  • Jimenez-Halla J.���Oscar���C., Sol�� Miquel: D��tz Benzannulation Reactions: Heteroatom and Substituent Effects in Chromium Fischer Carbene Complexes. Chem Eur J 2009, 15, 12503. <>
  • Aznar Fernando, Fañanás-Mastral Martín, Alonso Jorge, Fañanás Francisco J.: Diastereoselective Synthesis of Three-, Five-, Six-, and Seven-Membered Rings from Fischer Carbene Complexes and 4-Unsubstituted 1-Amino-1,3-Dienes. Chem. Eur. J. 2008, 14, 325. <>
  • Barluenga José, Fañanás-Mastral Martín, Aznar Fernando: CH Insertion Processes on Stabilized Indolyl and ortho-Aminophenyl Fischer Carbene Complexes: Synthesis of Azepino[3,2,1-hi] indole, Benzazepine and Indole Derivatives. Chem Eur J 2008, 14, 7508. <>
  • Sentets Stéphane, Serres Rémi, Ortin Yannick, Lugan Noël, Lavigne Guy: Directed Formation of Allene Complexes upon Reaction of Non-heteroatom-Substituted Manganese Alkynyl Carbene Complexes with Nucleophiles. Organometallics 2008, 27, 2078. <>
  • Granados Alejandro M., Fracaroli Alejandro M., de Rossi Rita H., Fuertes Pedro, Torroba Tomás: Alkynyl Fischer carbene complex as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene: synthesis of E-dithiafulvene thione and dithioesters. Chem Commun 2008, 483. <>
  • Chakraborty Amarnath, Maishal Tarun K.: Promoting Effect of Imidazolium Ionic Liquid in the Reaction of Chromium Carbene Complexes with Alkynes: A Most Simple and Convenient Way to Get Demetallated-Product!. Adv Synth Catal 2007, 349, 2435. <>
  • Nitsche Frank, Aumann Rudolf, Fröhlich Roland: Thiocarbene and alkoxycarbene tungsten complexes exhibit typically different reaction paths. J Organomet Chem 2007, 692, 2971. <>
  • Gu Kaichun, Yang Gang, Zhang Weiping, Liu Xiumei, Yu Zhengkun, Han Xiuwen, Bao Xinhe: An experimental–theoretical approach to the kinetics and mechanism of Michael type addition: α,β-Unsaturated tungsten Fischer carbene complex as the substrate. J Organomet Chem 2006, 691, 1984. <>
  • Barluenga José, Alonso Jorge, Fañanás Francisco J.: Diastereoselective Synthesis of Five- and Seven-Membered Rings by [2+2+1], [3+2], [3+2+2], and [4+3] Carbocyclization Reactions of β-Substituted (Alkenyl)(methoxy)carbene Complexes with Methyl Ketone Lithium Enolates. Chem Eur J 2005, 11, 4995. <>
  • Busetto Luigi, Zanotti Valerio: Carbene ligands in diiron complexes. J Organomet Chem 2005, 690, 5430. <>
  • Ortin Yannick, Lugan Noël, Mathieu René: Subtle reactivity patterns of non-heteroatom-substituted manganese alkynyl carbene complexes in the presence of phosphorus probes. Dalton Trans 2005, 1620. <>
  • Barluenga José, Alonso Jorge, Fañanás Francisco J., Borge Javier, García-Granda Santiago: Diastereoselective Synthesis of Cycloheptadienol Derivatives by a Formal [5+2] Carbocyclization Reaction of α,β,γ,δ-Diunsaturated (Methoxy)carbene Complexes with Methyl Ketone Lithium Enolates. Angew Chem 2004, 116, 5626. <>
  • Barluenga José, Alonso Jorge, Fañanás Francisco J., Borge Javier, García-Granda Santiago: Diastereoselective Synthesis of Cycloheptadienol Derivatives by a Formal [5+2] Carbocyclization Reaction of α,β,γ,δ-Diunsaturated (Methoxy)carbene Complexes with Methyl Ketone Lithium Enolates. Angew Chem Int Ed 2004, 43, 5510. <>
  • Herndon James W: The chemistry of the carbon–transition metal double and triple bond: annual survey covering the year 2002. Coord Chem Rev - 2004, 248, 3. <>
  • Plantevin Véronique, Wojcicki Andrew: Chemistry of Fischer-type rhenacyclobutadiene complexes. I. Deprotonation, addition/substitution of nucleophilic reagents at α-carbon, and insertion of heteroatoms into rhenium–carbon bonds. J Organomet Chem 2004, 689, 2000. <>
  • Barluenga Jose: Fischer Carbene Complexes. A New Tool for Heterocyclic Synthesis. ChemInform 2003, 34. <>
  • Albano Vincenzo G, Bordoni Silvia, Busetto Luigi, Marchetti Fabio, Monari Magda, Zanotti Valerio: CN coupling between μ-aminocarbyne and nitrile ligands promoted by tolylacetylide addition to [Fe2{μ-CN(Me)(Xyl)}(μ-CO)(CO)(NCCMe3)(Cp)2][SO3CF3]. J Organomet Chem 2003, 684, 37. <>