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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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  • Spillane William, Malaubier Jean-Baptiste: Sulfamic Acid and Its N- and O-Substituted Derivatives. Chem. Rev. 2014, 114, 2507. <http://dx.doi.org/10.1021/cr400230c>
  • Zhu Ming-Kui, Chen Yu-Chen, Loh Teck-Peng: Radical-Mediated Diamination of Alkenes with Phenylhydrazine and Azodicarboxylates: Highly Diastereoselective Synthesis of trans -Diamines from Cycloalkenes. Chem. Eur. J. 2013, 19, 5250. <http://dx.doi.org/10.1002/chem.201203832>
  • Matsuda Naoki, Hirano Koji, Satoh Tetsuya, Miura Masahiro: Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines. J. Am. Chem. Soc. 2013, 135, 4934. <http://dx.doi.org/10.1021/ja4007645>
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  • Röben Caren, Souto José A., Escudero-Adán Eduardo C., Muñiz Kilian: Oxidative Diamination Promoted by Dinuclear Iodine(III) Reagents. Org. Lett. 2013, 15, 1008. <http://dx.doi.org/10.1021/ol3034884>
  • Takeda Youhei, Murakami Yuta, Ikeda Yuki, Minakata Satoshi: Nucleophilic Ring-Opening of N -o- Nosylaziridines with N- Chloro-N -Sodiocarbamate: Facile Preparation of Differentially Protected Vicinal Diamines. Asian Journal of Organic Chemistry 2012, 1, 226. <http://dx.doi.org/10.1002/ajoc.201200070>
  • Souto José A., González Yolanda, Iglesias Alvaro, Zian Debora, Lishchynskyi Anton, Muñiz Kilian: Iodine(III)-Promoted Intermolecular Diamination of Alkenes. Chem —Asian J 2012, 7, 1103. <http://dx.doi.org/10.1002/asia.201101025>
  • De Jong Sam, Nosal Daniel G., Wardrop Duncan J.: Methods for direct alkene diamination, new & old. Tetrahedron 2012, 68, 4067. <http://dx.doi.org/10.1016/j.tet.2012.03.036>
  • Chávez Patricia, Kirsch Jonathan, Streuff Jan, Muñiz Kilian: Palladium-Catalyzed Intramolecular Diamination of Acrylic Esters Using Sulfamates as Nitrogen Source. J Org Chern 2012, 77, 1922. <http://dx.doi.org/10.1021/jo202507d>
  • Müller Christian H., Fröhlich Roland, Daniliuc Constantin G., Hennecke Ulrich: Efficient Synthesis of Chiral 2,2′-Bipyrrolidines by an anti-Selective Alkene Diamination. Org. Lett. 2012, 14, 5944. <http://dx.doi.org/10.1021/ol302855z>
  • Chávez Patricia, Kirsch Jonathan, Hövelmann Claas H., Streuff Jan, Martínez-Belmonte Marta, Escudero-Adán Eduardo C., Martin Eddy, Muñiz Kilian: Metal-free diamination of alkenes employing bromide catalysis. Chem. Sci. 2012, 3, 2375. <http://dx.doi.org/10.1039/c2sc20242e>
  • 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 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>