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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1089-1096

http://dx.doi.org/10.1351/pac200880051089

First palladium- and nickel-catalyzed oxidative diamination of alkenes: Cyclic urea, sulfamide, and guanidine building blocks

Kilian Muñiz, Claas H. Hövelmann, Jan Streuff and Esther Campos-Gómez

Laboratory for Homogeneous Catalysis and Molecular Synthesis, Institute of Chemistry, UMR 7177, Université Louis Pasteur, 4 rue Blaise Pascal, F-67000 Strasbourg Cedex, France

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  • Chávez Patricia, Kirsch Jonathan, Streuff Jan, Muñiz Kilian: Palladium-Catalyzed Intramolecular Diamination of Acrylic Esters Using Sulfamates as Nitrogen Source. J Org Chern 2012, 120207105916009. <http://dx.doi.org/10.1021/jo202507d>
  • Muñiz Kilian, Kirsch Jonathan, Chávez Patricia: Intermolecular Regioselective 1,2-Diamination of Allylic Ethers. Synth Catal 2011, 353, 689. <http://dx.doi.org/10.1002/adsc.201000813>
  • Röben Caren, Souto José A., González Yolanda, Lishchynskyi Anton, Muñiz Kilian: Enantioselektive metallfreie Diaminierung von Styrolen. angew chemie 2011, 123, 9650. <http://dx.doi.org/10.1002/ange.201103077>
  • Röben Caren, Souto José A., González Yolanda, Lishchynskyi Anton, Muñiz Kilian: Enantioselective Metal-Free Diamination of Styrenes. Angew Chem Int E 2011, 50, 9478. <http://dx.doi.org/10.1002/anie.201103077>
  • Beccalli Egle M., Broggini Gianluigi, Fasana Andrea, Rigamonti Micol: Palladium-catalyzed C–N bond formation via direct C–H bond functionalization. Recent developments in heterocyclic synthesis. J Organomet Chem 2011, 696, 277. <http://dx.doi.org/10.1016/j.jorganchem.2010.09.078>
  • Martínez-Asencio Ana, Ramón Diego J., Yus Miguel: N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: scope and mechanistic considerations. Tetrahedron [London] 2011, 67, 3140. <http://dx.doi.org/10.1016/j.tet.2011.02.075>
  • Zhao Baoguo, Peng Xingao, Zhu Yingguang, Ramirez Thomas A., Cornwall Richard G., Shi Yian: Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species. S J Am Chem Soc 2011, 133, 20890. <http://dx.doi.org/10.1021/ja207691a>
  • Cano Rafael, Ramón Diego J., Yus Miguel: Impregnated Ruthenium on Magnetite as a Recyclable Catalyst for the N-Alkylation of Amines, Sulfonamides, Sulfinamides, and Nitroarenes Using Alcohols as Electrophiles by a Hydrogen Autotransfer Process. J Org Chern 2011, 76, 5547. <http://dx.doi.org/10.1021/jo200559h>
  • McDonald Richard I., Stahl Shannon S.: Modular Synthesis of 1,2-Diamine Derivatives by Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides. Angew Chem 2010, 122, 5661. <http://dx.doi.org/10.1002/ange.200906342>
  • Sequeira Fatima C., Turnpenny Benjamin W., Chemler Sherry R.: Copper-Promoted and Copper-Catalyzed Intermolecular Alkene Diamination. Angew Chem 2010, 122, 6509. <http://dx.doi.org/10.1002/ange.201003499>
  • Iglesias Álvaro, Pérez Edwin G., Muñiz Kilian: Eine intermolekulare Palladium-katalysierte vicinale Diaminierung von nichtaktivierten Alkenen. Angew Chem 2010, 122, 8286. <http://dx.doi.org/10.1002/ange.201003653>
  • McDonald Richard I., Stahl Shannon S.: Modular Synthesis of 1,2-Diamine Derivatives by Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides. Angew Chem Int Ed 2010, 49, 5529. <http://dx.doi.org/10.1002/anie.200906342>
  • Sequeira Fatima C., Turnpenny Benjamin W., Chemler Sherry R.: Copper-Promoted and Copper-Catalyzed Intermolecular Alkene Diamination. Angew Chem Int Ed 2010, 49, 6365. <http://dx.doi.org/10.1002/anie.201003499>
  • Iglesias Álvaro, Pérez Edwin G., Muñiz Kilian: An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes. Angew Chem Int Ed 2010, 49, 8109. <http://dx.doi.org/10.1002/anie.201003653>
  • Martínez-Asencio Ana, Ramón Diego J., Yus Miguel: N-Alkylation of poor nucleophilic amine and sulfonamide derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate. Tetrahetron Lett 2010, 51, 325. <http://dx.doi.org/10.1016/j.tetlet.2009.11.009>
  • Zhao Baoguo, Peng Xingao, Cui Sunliang, Shi Yian: Cu(I)-Catalyzed Regioselective Diamination of Conjugated Dienes via Dual Mechanistic Pathways. J Am Chem Soc 2010, 132, 11009. <http://dx.doi.org/10.1021/ja103838d>
  • Oloo Williamson, Zavalij Peter Y., Zhang Jing, Khaskin Eugene, Vedernikov Andrei N.: Preparation and C−X Reductive Elimination Reactivity of Monoaryl PdIV−X Complexes in Water (X = OH, OH2, Cl, Br). J Am Chem Soc 2010, 132, 14400. <http://dx.doi.org/10.1021/ja107185w>
  • Zhao Baoguo, Du Haifeng, Cui Sunliang, Shi Yian: Synthetic and Mechanistic Studies on Pd(0)-Catalyzed Diamination of Conjugated Dienes. J Am Chem Soc 2010, 132, 3523. <http://dx.doi.org/10.1021/ja909459h>
  • Rosewall Carolyn F., Sibbald Paul A., Liskin Dmitry V., Michael Forrest E.: Palladium-Catalyzed Carboamination of Alkenes Promoted by N-Fluorobenzenesulfonimide via C−H Activation of Arenes. J Am Chem Soc 2009, 131, 9488. <http://dx.doi.org/10.1021/ja9031659>
  • Sibbald Paul A., Rosewall Carolyn F., Swartz Rodney D., Michael Forrest E.: Mechanism of N-Fluorobenzenesulfonimide Promoted Diamination and Carboamination Reactions: Divergent Reactivity of a Pd(IV) Species. J Am Chem Soc 2009, 131, 15945. <http://dx.doi.org/10.1021/ja906915w>
  • Martínez Ricardo, Ramón Diego J., Yus Miguel: Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite. Org Biomol Chem 2009, 7, 2176. <http://dx.doi.org/10.1039/b901929d>
  • Muniz Kilian, Hovelmann Claas H., Streuff Jan, Campos-Gomez Esther: ChemInform Abstract: First Palladium- and Nickel-Catalyzed Oxidative Diamination of Alkenes: Cyclic Urea, Sulfamide, and Guanidine Building Blocks. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843239>