Mesoionic 1,2,3-Triazoles and 1,2,3-Triazole Carbenes

作者: Jesus M. Aizpurua , Maialen Sagartzazu-Aizpurua , Zaira Monasterio

DOI: 10.1007/7081_2014_120

关键词: CycloadditionChemistryHomogeneous catalysisDenticityTransmetalationCovalent bondCarbeneMesoionic1,2,3-TriazoleCombinatorial chemistry

摘要: Routine access to 1,2,3-triazoles through the copper-catalyzed azide-alkyne “click” cycloaddition reaction has promoted rapid development of 1,2,3-triazolylidenes as ligands for transition metals. The organometallic complexes containing this kind N-heterocyclic carbene (NHCs) have shown possess unique structural characteristics, including a relatively high covalent contribution metal–NHC bond, strong donor ability, and mesoionic character. Complexes triazolylidene carbenes (MICs) are readily available, among other methods, by metallation N3-substituted 1,2,3-triazolium salts, usually followed transmetallation reactions. A diverse array monodentate, polydentate, bridged 1,2,3-triazolylidene motif been described, structures them characterized in detail. Promising applications catalysis involving C–C C–X bond formation redox reactions emerged recent years metal complexes, and, owing modular multiple functionalization possibilities around 1,2,3-triazole scaffold, novel expected upcoming years.

参考文章(93)
Min Weng, Armin Geyer, Anke Friemel, J. C. Jochims, Martin Lutz, Cycloaddition Reactions of 1,3‐Diaza‐2‐azoniaallene Salts and Glycals Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 342, pp. 486- 493 ,(2000) , 10.1002/1521-3897(200006)342:5<486::AID-PRAC486>3.0.CO;2-S
Jesus Aizpurua, Maialen Sagartzazu-Aizpurua, Itxaso Azcune, José Miranda, Zaira Monasterio, Eva García-Lecina, Raluca Fratila, ‘Click’ Synthesis of Nonsymmetrical 4,4′-Bis(1,2,3-triazolium) Salts Synthesis. ,vol. 2011, pp. 2737- 2742 ,(2011) , 10.1055/S-0030-1260061
Ana Petronilho, James A. Woods, Stefan Bernhard, Martin Albrecht, Bimetallic Iridium–Carbene Complexes with Mesoionic Triazolylidene Ligands for Water Oxidation Catalysis European Journal of Inorganic Chemistry. ,vol. 2014, pp. 708- 714 ,(2014) , 10.1002/EJIC.201300843
Joseph C. Y. Lin, Roy T. W. Huang, Chen S. Lee, Amitabha Bhattacharyya, Wen S. Hwang, Ivan J. B. Lin, Coinage Metal−N-Heterocyclic Carbene Complexes Chemical Reviews. ,vol. 109, pp. 3561- 3598 ,(2009) , 10.1021/CR8005153
Han Vinh Huynh, Yuan Han, Ramasamy Jothibasu, Jie An Yang, 13C NMR Spectroscopic Determination of Ligand Donor Strengths Using N-Heterocyclic Carbene Complexes of Palladium(II) Organometallics. ,vol. 28, pp. 5395- 5404 ,(2009) , 10.1021/OM900667D
Lucile Bernet, Ralte Lalrempuia, Wadih Ghattas, Helge Mueller-Bunz, Laura Vigara, Antoni Llobet, Martin Albrecht, Tunable single-site ruthenium catalysts for efficient water oxidation Chemical Communications. ,vol. 47, pp. 8058- 8060 ,(2011) , 10.1039/C1CC12615F
Guy Bertrand, Jean Bouffard, Benjamin K. Keitz, Ralf Tonner, Gregorio Guisado-Barrios, Gernot Frenking, Robert H. Grubbs, Synthesis of Highly Stable 1,3-Diaryl-1H-1,2,3-triazol-5-ylidenes and their Applications in Ruthenium-Catalyzed Olefin Metathesis Organometallics. ,vol. 30, pp. 2617- 2627 ,(2011) , 10.1021/OM200272M
Paulson Mathew, Antonia Neels, Martin Albrecht, 1,2,3-Triazolylidenes as Versatile Abnormal Carbene Ligands for Late Transition Metals Journal of the American Chemical Society. ,vol. 130, pp. 13534- 13535 ,(2008) , 10.1021/JA805781S
Hiroshi Inomata, Kenichi Ogata, Shin-ichi Fukuzawa, Zhaomin Hou, Direct C–H Carboxylation with Carbon Dioxide Using 1,2,3-Triazol-5-ylidene Copper(I) Complexes Organic Letters. ,vol. 14, pp. 3986- 3989 ,(2012) , 10.1021/OL301760N