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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 249-256

http://dx.doi.org/10.1351/pac200678020249

Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base pair model

Bernhard Breit and Wolfgang Seiche

Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg, Germany

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  • Fuchs Daniela, Rousseau Géraldine, Diab Lisa, Gellrich Urs, Breit Bernhard: Tandem Rhodium-Catalyzed Hydroformylation-Hydrogenation of Alkenes by Employing a Cooperative Ligand System. angew chemie 2012, 124, 2220. <http://dx.doi.org/10.1002/ange.201108946>
  • Fuchs Daniela, Rousseau Géraldine, Diab Lisa, Gellrich Urs, Breit Bernhard: Tandem Rhodium-Catalyzed Hydroformylation-Hydrogenation of Alkenes by Employing a Cooperative Ligand System. Angew Chem Int E 2012, 51, 2178. <http://dx.doi.org/10.1002/anie.201108946>
  • Pignataro Luca, Bovio Chiara, Civera Monica, Piarulli Umberto, Gennari Cesare: A Library Approach to the Development of BenzaPhos: Highly Efficient Chiral Supramolecular Ligands for Asymmetric Hydrogenation. Chem. Eur. J. 2012, 18, 10368. <http://dx.doi.org/10.1002/chem.201201032>
  • Legrand François-Xavier, Menuel Stéphane, Bricout Hervé, Tilloy Sébastien, Monflier Eric, Tran Diem Ngan: Cyclodextrin–phosphane possessing a guest-tunable conformation for aqueous rhodium-catalyzed hydroformylation. Chem Commn 2012, 48, 753. <http://dx.doi.org/10.1039/c1cc16326d>
  • Lloret Fillol Julio, Kruckenberg Achim, Scherl Peter, Wadepohl Hubert, Gade Lutz H.: Stitching Phospholanes Together Piece by Piece: New Modular Di- and Tridentate Stereodirecting Ligands. Chemistry A European Journal 2011, 17, 14047. <http://dx.doi.org/10.1002/chem.201101864>
  • Carboni Stefano, Gennari Cesare, Pignataro Luca, Piarulli Umberto: Supramolecular ligand–ligand and ligand–substrate interactions for highly selective transition metal catalysis. Dalton Trans 2011, 40, 4355. <http://dx.doi.org/10.1039/c0dt01517b>
  • Wieland Joerg, Breit Bernhard: A combinatorial approach to the identification of self-assembled ligands for rhodium-catalysed asymmetric hydrogenation. Nature Chem 2010, 2, 832. <http://dx.doi.org/10.1038/nchem.800>
  • Laungani Andy C., Keller Manfred, Slattery John M., Krossing Ingo, Breit Bernhard: Cooperative Effect of a Classical and a Weak Hydrogen Bond for the Metal-Induced Construction of a Self-Assembled β-Turn Mimic. Chem Eur J 2009, 15, 10405. <http://dx.doi.org/10.1002/chem.200900662>
  • Goudriaan P. Elsbeth, Kuil Mark, Jiang Xiao-Bin, van Leeuwen Piet W. N. M., Reek Joost N. H.: SUPRAPhos ligands for the regioselective rhodium catalyzed hydroformylation of styrene forming the linear aldehyde. Dalton Trans 2009, 1801. <http://dx.doi.org/10.1039/b818665k>
  • Rubio Miguel, Jellema Erica, Siegler Maxime A., Spek Anthony L., Reek Joost N. H., de Bruin Bas: Supramolecular NHC ligands: on the influence of ZnII-templates on the activity of RhI(cod) complexes in ‘carbene polymerization’. Dalton Trans 2009, 8970. <http://dx.doi.org/10.1039/b911339h>
  • Reetz Manfred T.: Kombinatorische Übergangsmetallkatalyse: Mischungen einzähniger Liganden zur Kontrolle der Enantio-, Diastereo- und Regioselektivität. Angew Chem 2008, 120, 2592. <http://dx.doi.org/10.1002/ange.200704327>
  • Reetz Manfred T.: Combinatorial Transition-Metal Catalysis: Mixing Monodentate Ligands to Control Enantio-, Diastereo-, and Regioselectivity. Angew Chem Int Ed 2008, 47, 2556. <http://dx.doi.org/10.1002/anie.200704327>
  • Laungani Andy C., Slattery John M., Krossing Ingo, Breit Bernhard: Supramolecular Bidentate Ligands by Metal-Directed in situ Formation of Antiparallel β-Sheet Structures and Application in Asymmetric Catalysis. Chem Eur J 2008, 14, 4488. <http://dx.doi.org/10.1002/chem.200800359>
  • Goudriaan P. Elsbeth, van Leeuwen Piet W. N. M., Birkholz Mandy‐Nicole, Reek Joost N. H.: Libraries of Bidentate Phosphorus Ligands; Synthesis Strategies and Application in Catalysis. Eur J Inorg Chem 2008, 2008, 2939. <http://dx.doi.org/10.1002/ejic.200800139>
  • Goudriaan P. Elsbeth, Jang Xiao-Bin, Kuil Mark, Lemmens Renske, Van Leeuwen Piet W. N. M., Reek Joost N. H.: Synthesis of Building Blocks for the Development of the SUPRAPhos Ligand Library and Examples of Their Application in Catalysis. Eur J Org Chem 2008, 2008, 6079. <http://dx.doi.org/10.1002/ejoc.200800499>
  • Schäffner Benjamin, Holz Jens, Verevkin Sergey P., Börner Armin: Rhodium-catalyzed asymmetric hydrogenation with self-assembling catalysts in propylene carbonate. Tetrahetron Lett 2008, 49, 768. <http://dx.doi.org/10.1016/j.tetlet.2007.11.199>
  • Laungani Andy Ch., Breit Bernhard: Supramolecular PhanePhos-analogous ligands through hydrogen-bonding for asymmetric hydrogenation. Chem Commun 2008, 844. <http://dx.doi.org/10.1039/b716529c>
  • Dubrovina Natalia V., Shuklov Ivan A., Birkholz Mandy-Nicole, Michalik Dirk, Paciello Rocco, Börner Armin: Fluorinated Alcohols as Solvents for Enantioselective Hydrogenation with Chiral Self-Assembling Rhodium Catalysts. Adv Synth Catal 2007, 349, 2183. <http://dx.doi.org/10.1002/adsc.200700177>
  • Machut Cécile, Patrigeon Julien, Tilloy Sébastien, Bricout Hervé, Hapiot Frédéric, Monflier Eric: Self-Assembled Supramolecular Bidentate Ligands for Aqueous Organometallic Catalysis. Angew Chem 2007, 119, 3100. <http://dx.doi.org/10.1002/ange.200605166>
  • Waloch Christoph, Wieland Jörg, Keller Manfred, Breit Bernhard: Self-Assembly of Bidentate Ligands for Combinatorial Homogeneous Catalysis: Methanol-Stable Platforms Analogous to the Adenine–Thymine Base Pair. Angew Chem 2007, 119, 3097. <http://dx.doi.org/10.1002/ange.200605202>
  • Machut Cécile, Patrigeon Julien, Tilloy Sébastien, Bricout Hervé, Hapiot Frédéric, Monflier Eric: Self-Assembled Supramolecular Bidentate Ligands for Aqueous Organometallic Catalysis. Angew Chem Int Ed 2007, 46, 3040. <http://dx.doi.org/10.1002/anie.200605166>
  • Waloch Christoph, Wieland Jörg, Keller Manfred, Breit Bernhard: Self-Assembly of Bidentate Ligands for Combinatorial Homogeneous Catalysis: Methanol-Stable Platforms Analogous to the Adenine–Thymine Base Pair. Angew Chem Int Ed 2007, 46, 3037. <http://dx.doi.org/10.1002/anie.200605202>
  • Birkholz Mandy-Nicole, Dubrovina Natalia V., Jiao Haijun, Michalik Dirk, Holz Jens, Paciello Rocco, Breit Bernhard, Börner Armin: Enantioselective Hydrogenation with Self-Assembling Rhodium Phosphane Catalysts: Influence of Ligand Structure and Solvent. Chem Eur J 2007, 13, 5896. <http://dx.doi.org/10.1002/chem.200601607>
  • Slagt Vincent F., Kaiser Patrick, Berkessel Albrecht, Kuil Mark, Kluwer Alexander M., van Leeuwen Piet W. N. M., Reek Joost N. H.: Fine-Tuning Ligands for Catalysis Using Supramolecular Strategies. Eur J Inorg Chem 2007, 2007, 4653. <http://dx.doi.org/10.1002/ejic.200700550>
  • Birkholz Mandy-Nicole, Dubrovina Natalia V., Shuklov Ivan A., Holz Jens, Paciello Rocco, Waloch Christoph, Breit Bernhard, Börner Armin: Enantioselective Pd-catalyzed allylic amination with self-assembling and non-assembling monodentate phosphine ligands. Tet Asymm 2007, 18, 2055. <http://dx.doi.org/10.1016/j.tetasy.2007.08.026>
  • Kuil Mark, Goudriaan P. Elsbeth, Kleij Arjan W., Tooke Duncan M., Spek Anthony L., van Leeuwen Piet W. N. M., Reek Joost N. H.: Rigid bis-zinc(ii) salphen building blocks for the formation of template-assisted bidentate ligands and their application in catalysis. Dalton Trans 2007, 2311. <http://dx.doi.org/10.1039/b702375h>
  • Breit Bernhard, Seiche Wolfgang: Self-Assembly of Bidentate Ligands for Combinatorial Homogeneous Catalysis Based on an A—T Base Pair Model. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200631259>
  • Sandee Albertus J., Reek Joost N. H.: Bidentate ligands by supramolecular chemistry?the future for catalysis?. Dalton Trans 2006, 3385. <http://dx.doi.org/10.1039/b606045p>