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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 507-516

http://dx.doi.org/10.1351/pac200476030507

Development of catalysts for the hydroamination of olefins

J. F. Hartwig

Department of Chemistry, Yale University, P.O.Box 208107, New Haven, CT 06520-8107, USA

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  • Susanti Dewi, Ng Linda Li Ru, Chan Philip Wai Hong: Silica Gel-Mediated Hydroamination/Semipinacol Rearrangement of 2-Alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-Oxindoles from Alkynes and 1-(2-Aminophenyl) Ketones. Adv. Synth. Catal. 2014, 356, 353. <http://dx.doi.org/10.1002/adsc.201300911>
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  • Emer Enrico, Pfeifer Lukas, Brown John M., Gouverneur Véronique: cis -Specific Hydrofluorination of Alkenylarenes under Palladium Catalysis through an Ionic Pathway. Angew. Chem. Int. Ed. 2014, 53, 4181. <http://dx.doi.org/10.1002/anie.201310056>
  • Nirmala M., Manikandan R., Prakash G., Viswanathamurthi P.: Ruthenium(II) complexes of hybrid 8-hydroxyquinoline-thiosemicarbazone ligands: synthesis, characterization and catalytic applications. Appl. Organometal. Chem. 2014, 28, 18. <http://dx.doi.org/10.1002/aoc.3052>
  • Ciobanu M., Tirsoaga A., Amoros P., Beltran D., Coman S.M., Parvulescu V.I.: Comparative hydroamination of aniline and substituted anilines with styrene on different zeolites, triflate based catalysts and their physical mixtures. Applied Catalysis A: General 2014, 474, 230. <http://dx.doi.org/10.1016/j.apcata.2013.05.032>
  • Prakash Govindan, Viswanathamurthi Periasamy: New ruthenium(II) carbonyl complexes bearing disulphide Schiff base ligands and their applications as catalyst for some organic transformations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014. <http://dx.doi.org/10.1016/j.saa.2014.03.086>
  • Wang Yu-Mei, Li Ting-Ting, Liu Gong-Qing, Zhang Li, Duan Lili, Li Lin, Li Yue-Ming: Cooperative effect in organocatalytic intramolecular hydroamination of unfunctionalized olefins. RSC Adv. 2014, 4, 9517. <http://dx.doi.org/10.1039/c3ra47060a>
  • Barros M. Teresa, Dey Suvendu S., Maycock Christopher D.: Metal-Free Synthesis of Secondary Arylamines: An Aliphatic-to-Aromatic Transformation. Eur. J. Org. Chem. 2013, 2013, 742. <http://dx.doi.org/10.1002/ejoc.201201263>
  • Ramachandran Rangasamy, Viswanathamurthi Periasamy: Ruthenium(II) carbonyl complexes containing pyridine carboxamide ligands and PPh3/AsPh3/Py coligands: Synthesis, spectral characterization, catalytic and antioxidant studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013, 103, 53. <http://dx.doi.org/10.1016/j.saa.2012.10.072>
  • Zeng Xiaoming: Recent Advances in Catalytic Sequential Reactions Involving Hydroelement Addition to Carbon–Carbon Multiple Bonds. Chem. Rev. 2013, 113, 6864. <http://dx.doi.org/10.1021/cr400082n>
  • Ghatak Kamalika, Mane Manoj, Vanka Kumar: Metal or Nonmetal Cooperation with a Phenyl Group: Route to Catalysis? A Computational Investigation. ACS Catal. 2013, 3, 920. <http://dx.doi.org/10.1021/cs400174u>
  • Dang Tuan Thanh, Ramalingam Balamurugan, Shan Siah Pei, Seayad Abdul Majeed: An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols. ACS Catal. 2013, 3, 2536. <http://dx.doi.org/10.1021/cs400799n>
  • Armanino Nicolas, Carreira Erick M.: Ruthenium-Catalyzed Intramolecular Hydrocarbamoylation of Allylic Formamides: Convenient Access to Chiral Pyrrolidones. J. Am. Chem. Soc. 2013, 135, 6814. <http://dx.doi.org/10.1021/ja4026787>
  • Dion Isabelle, Vincent-Rocan Jean-François, Zhang Lei, Cebrowski Pamela H., Lebrun Marie-Eve, Pfeiffer Jennifer Y., Bédard Anne-Catherine, Beauchemin André M.: Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products. J. Org. Chem. 2013, 78, 12735. <http://dx.doi.org/10.1021/jo4023149>
  • Li Shengkun, Huang Kexuan, Zhang Jiwen, Wu Wenjun, Zhang Xumu: Rhodium-Catalyzed Highly Regioselective Hydroaminomethylation of Styrenes with Tetraphosphorus Ligands. Org. Lett. 2013, 15, 3078. <http://dx.doi.org/10.1021/ol4012635>
  • Reznichenko Alexander L., Hultzsch Kai C.: C1-Symmetric Rare-Earth-Metal Aminodiolate Complexes for Intra- and Intermolecular Asymmetric Hydroamination of Alkenes. Organometallics 2013, 32, 1394. <http://dx.doi.org/10.1021/om3010614>
  • Sharma Sumeet K., Lynch James, Sobolewska Anna M., Plucinski Pawel, Watson Robert J., Williams Jonathan M. J.: Pt/C catalysed direct reductive amination of nitriles with primary amines in a continuous flow multichannel microreactor. Catal. Sci. Technol. 2013, 3, 85. <http://dx.doi.org/10.1039/c2cy20431b>
  • Chen Qian, Lv Lanlan, Yu Meng, Shi Yanhui, Li Yuling, Pang Guangsheng, Cao Changsheng: Simple, efficient and reusable Pd–NHC catalysts for hydroamination. RSC Adv. 2013, 3, 18359. <http://dx.doi.org/10.1039/c3ra42990c>
  • Kretschmer Robert, Schlangen Maria, Schwarz Helmut: C-N- und C-C-Bindungsknüpfung in der Reaktion von “nacktem” Ni(NH2)+ mit C2H4: Mechanistische Erkenntnisse über die metallvermittelte Hydroaminierung eines nichtaktivierten Olefins. angew chemie 2012, 124, 3541. <http://dx.doi.org/10.1002/ange.201104433>
  • Kretschmer Robert, Schlangen Maria, Schwarz Helmut: CN and CC Bond Formations in the Thermal Reactions of “Bare” Ni(NH2)+ with C2H4: Mechanistic Insight on the Metal-Mediated Hydroamination of an Unactivated Olefin. Angew Chem Int E 2012, 51, 3483. <http://dx.doi.org/10.1002/anie.201104433>
  • Tobisch Sven: Metal-Ligand Cooperation in Catalytic Intramolecular Hydroamination: A Computational Study of Iridium-Pyrazolato Cooperative Activation of Aminoalkenes. Chem. Eur. J. 2012, 18, 7248. <http://dx.doi.org/10.1002/chem.201103620>
  • Benndorf Paul, Kratsch Jochen, Hartenstein Larissa, Preuss Corinna M., Roesky Peter W.: Chiral Benzamidinate Ligands in Rare-Earth-Metal Coordination Chemistry. Chem. Eur. J. 2012, 18, 14454. <http://dx.doi.org/10.1002/chem.201202457>
  • Sarcher Christian, Lühl Anja, Falk Florian C., Lebedkin Sergei, Kühn Michael, Wang Cong, Paradies Jan, Kappes Manfred M., Klopper Wim, Roesky Peter W.: [2.2]Paracyclophanediyldiphosphane Complexes of Gold. Eur. J. Inorg. Chem. 2012, 2012, 5033. <http://dx.doi.org/10.1002/ejic.201200751>
  • Li Lei, Huang Genping, Chen Zhou, Liu Wei, Wang Xiufang, Chen Yanmei, Yang Lijuan, Li Wu, Li Yahong: Gallium Trichloride Catalyzed Hydroamination of Alkynes: Scope, Limitation, and Mechanistic Studies by DFT. Eur. J. Org. Chem. 2012, 2012, 5564. <http://dx.doi.org/10.1002/ejoc.201200829>
  • Wang Feijun, Liu Lian-jun, Wang Wenfeng, Li Shengke, Shi Min: Chiral NHC���metal-based asymmetric catalysis. Coordination Chemistry Reviews 2012, 256, 804. <http://dx.doi.org/10.1016/j.ccr.2011.11.013>
  • Cervera-Padrell Albert E., Skovby Tommy, Kiil Søren, Gani Rafiqul, Gernaey Krist V.: Active pharmaceutical ingredient (API) production involving continuous processes – A process system engineering (PSE)-assisted design framework. European Journal of Pharmaceutics and Biopharmaceutics 2012, 82, 437. <http://dx.doi.org/10.1016/j.ejpb.2012.07.001>
  • Samblanet Danielle C., Schmidt Joseph A.R.: Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride. Journal of Organometallic Chemistry 2012, 720, 7. <http://dx.doi.org/10.1016/j.jorganchem.2012.08.027>
  • Patil Nitin T., Kavthe Rahul D., Shinde Valmik S.: Transition metal-catalyzed addition of C-, N- and O-nucleophiles to unactivated C–C multiple bonds. Tetrahedron 2012, 68, 8079. <http://dx.doi.org/10.1016/j.tet.2012.05.125>
  • Chang Meng-Yang, Wu Ming-Hao, Chen Yeh-Long: Synthesis of dihydrobenzoimidazo[2,1-a]isoquinolines. Tetrahedron Letters 2012, 53, 4156. <http://dx.doi.org/10.1016/j.tetlet.2012.05.132>
  • Tobisch Sven: Intramolecular Aminoalkene Hydroamination Mediated by a Tethered Bis(ureate)zirconium Complex: Computational Perusal of Various Pathways for Aminoalkene Activation. Inrog Chem 2012, 51, 3786. <http://dx.doi.org/10.1021/ic202753m>
  • Trambitas Alexandra G., Melcher Daniel, Hartenstein Larissa, Roesky Peter W., Daniliuc Constantin, Jones Peter G., Tamm Matthias: Bis(imidazolin-2-iminato) Rare Earth Metal Complexes: Synthesis, Structural Characterization, and Catalytic Application. Inorg. Chem. 2012, 51, 6753. <http://dx.doi.org/10.1021/ic300407u>
  • Susanti Dewi, Koh Fujiet, Kusuma Jeffrey Antonius, Kothandaraman Prasath, Chan Philip Wai Hong: Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols. J. Org. Chem. 2012, 77, 7166. <http://dx.doi.org/10.1021/jo301198z>
  • Agrawal Santosh, Lenormand Maud, Martín-Matute Belén: Selective Alkylation of (Hetero)Aromatic Amines with Alcohols Catalyzed by a Ruthenium Pincer Complex. Z Org Lett 2012, 14, 1456. <http://dx.doi.org/10.1021/ol3001969>
  • Hua Carol, Vuong Khuong Q., Bhadbhade Mohan, Messerle Barbara A.: New Rhodium(I) and Iridium(I) Complexes Containing Mixed Pyrazolyl–1,2,3-Triazolyl Ligands As Catalysts for Hydroamination. Organomettalics 2012, 31, 1790. <http://dx.doi.org/10.1021/om201171b>
  • Gehrmann Thorsten, Plundrich Gudrun T., Wadepohl Hubert, Gade Lutz H.: [2 + 2] Cycloaddition Products of Zirconium and Hafnium Hydrazinediides with Allenes and Heteroallenes and Their Thermally Induced Rearrangements. Organomettalics 2012, 31, 3346. <http://dx.doi.org/10.1021/om300143h>
  • Feller Moran, Diskin-Posner Yael, Shimon Linda J. W., Ben-Ari Eyal, Milstein David: N–H Activation by Rh(I) via Metal–Ligand Cooperation. Organometallics 2012, 31, 4083. <http://dx.doi.org/10.1021/om300248r>
  • Lühl Anja, Hartenstein Larissa, Blechert Siegfried, Roesky Peter W.: Comparison of Decamethyldizincocene [(η5-Cp*)2Zn2] versus Decamethylzincocene [Cp*2Zn] and Diethylzinc Et2Zn As Precatalysts for the Intermolecular Hydroamination Reaction. Organometallics 2012, 31, 7109. <http://dx.doi.org/10.1021/om300649q>
  • Tobisch Sven: Mechanistic elucidation of the yttrium(iii)-catalysed intramolecular aminoalkene hydroamination: DFT favours a stepwise σ-insertive mechanism. Dalton Trans. 2012, 41, 9182. <http://dx.doi.org/10.1039/c2dt30814b>
  • Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine. angew chemie 2011, 123, 5674. <http://dx.doi.org/10.1002/ange.201100740>
  • Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine. Angew. Chem. Int. Ed. 2011, 50, 5560. <http://dx.doi.org/10.1002/anie.201100740>
  • Ananikov Valentine P., Beletskaya Irina P.: Alkyne Insertion into the MP and MH Bonds (M=Pd, Ni, Pt, and Rh): A Theoretical Mechanistic Study of the CP and CH Bond-Formation Steps. Chem Asian J 2011, 6, 1423. <http://dx.doi.org/10.1002/asia.201000840>
  • Liu Yong, Chen Wen, Feng Chao, Deng Guojun: Ruthenium-Catalyzed One-Pot Aromatic Secondary Amine Formation from Nitroarenes and Alcohols. Chem. Asian J. 2011, 6, 1142. <http://dx.doi.org/10.1002/asia.201000945>
  • Norinder Jakob, Börner Armin: Highly Efficient and Selective Catalytic N-Alkylation of Amines with Alcohols in Water. ChemCatChem 2011, 3, 1407. <http://dx.doi.org/10.1002/cctc.201100197>
  • Tobisch Sven: Does a Concerted Non-Insertive Mechanism Prevail over a σ-Insertive Mechanism in Catalytic Cyclohydroamination by Magnesium Tris(oxazolinyl)phenylborate Compounds? A Computational Study. Chemistry A European Journal 2011, 17, 14974. <http://dx.doi.org/10.1002/chem.201101490>
  • Khamwong Chaleowsak, Sakee Uthai: Palladium-catalyzed hydroamination of C-(tetra-O-acetyl-β-d-galactopyranosyl)allene. Carbohydrates Research 2011, 346, 334. <http://dx.doi.org/10.1016/j.carres.2010.11.006>
  • Xu Tao, Qiu Shuifa, Liu Guosheng: Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant. J Organomet Chem 2011, 696, 46. <http://dx.doi.org/10.1016/j.jorganchem.2010.07.015>
  • Yi Chae S.: Recent advances in the synthetic and mechanistic aspects of the ruthenium-catalyzed carbon–heteroatom bond forming reactions of alkenes and alkynes. J Organomet Chem 2011, 696, 76. <http://dx.doi.org/10.1016/j.jorganchem.2010.08.002>
  • Shaffer Andrew R., Zingales Nicholas C., Beck John F., Schmidt Joseph A.R., Kuchenbeiser Glenn: Palladium(II) 3-iminophosphine (3IP) complexes: Active precatalysts for the intermolecular hydroamination of 1,2-dienes (allenes) and 1,3-dienes with aliphatic amines under mild conditions. J Organomet Chem 2011, 696, 179. <http://dx.doi.org/10.1016/j.jorganchem.2010.08.033>
  • Basuli Falguni, Wicker Benjamin, Huffman John C., Mindiola Daniel J.: Understanding the role of an easy-to-prepare aldimine–alkyne carboamination catalyst, [Ti(NMe2)3(NHMe2)][B(C6F5)4]. J Organomet Chem 2011, 696, 235. <http://dx.doi.org/10.1016/j.jorganchem.2010.09.017>
  • Vitanova Daniela V., Hampel Frank, Hultzsch Kai C.: Linked bis(β-diketiminato) yttrium and lanthanum complexes as catalysts in asymmetric hydroamination/cyclization of aminoalkenes (AHA). J Organomet Chem 2011, 696, 321. <http://dx.doi.org/10.1016/j.jorganchem.2010.09.051>
  • Ananikov Valentine P., Zalesskiy Sergey S., Kachala Vadim V., Beletskaya Irina P.: NMR approach for the identification of dinuclear and mononuclear complexes: The first detection of [Pd(SPh)2(PPh3)2] and [Pd2(SPh)4(PPh3)2] – The intermediate complexes in the catalytic carbon–sulfur bond formation reaction. J Organomet Chem 2011, 696, 400. <http://dx.doi.org/10.1016/j.jorganchem.2010.10.012>
  • Demir Serpil, Özdemir İsmail, Çetinkaya Bekir, Arslan Hakan, VanDerveer Don: Synthesis and characterization of bidentate NHC–Pd complexes and their role in amination reactions. J Polyhedron 2011, 30, 195. <http://dx.doi.org/10.1016/j.poly.2010.10.015>
  • Das Priyabrata, McLeod David, McNulty James: A direct synthesis of functionalized styrenes and terminal 1,3-dienes via aqueous Wittig chemistry with formalin. Tetrahedron Letters 2011, 52, 199. <http://dx.doi.org/10.1016/j.tetlet.2010.10.090>
  • Tobisch Sven: Mechanistic investigation of organolanthanide-mediated hydroamination of aminoallenes: A comprehensive computational assessment of various routes for allene activation. Dalton Trans 2011, 40, 249. <http://dx.doi.org/10.1039/c0dt00819b>
  • Rao Weidong, Kothandaraman Prasath, Koh Chii Boon, Chan Philip Wai Hong: Copper(II) Triflate-Catalyzed Intramolecular Hydroamination of Homoallylic Amino Alcohols as an Expedient Route to trans-2,5-Dihydro-1H-pyrroles and 1,2-Dihydroquinolines. Adv Synth Catal 2010, 352, 2521. <http://dx.doi.org/10.1002/adsc.201000450>
  • Ananikov Valentine P., Khemchyan Levon L., Beletskaya Irina P., Starikova Zoya A.: Acid-Free Nickel Catalyst for Stereo- and Regioselective Hydrophosphorylation of Alkynes: Synthetic Procedure and Combined Experimental and Theoretical Mechanistic Study. Adv Synth Catal 2010, 352, 2979. <http://dx.doi.org/10.1002/adsc.201000606>
  • Zeng Xiaoming, Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of Alkynes. Angew Chem 2010, 122, 954. <http://dx.doi.org/10.1002/ange.200905341>
  • Melaimi Mohand, Soleilhavoup Michèle, Bertrand Guy: Stabile cyclische Carbene und verwandte Spezies jenseits der Diaminocarbene. Angew Chem 2010, 122, 8992. <http://dx.doi.org/10.1002/ange.201000165>
  • Reznichenko Alexander L., Nguyen Hiep N., Hultzsch Kai C.: Asymmetrische intermolekulare Hydroaminierung nichtaktivierter Alkene mit einfachen Aminen. Angew Chem 2010, 122, 9168. <http://dx.doi.org/10.1002/ange.201004570>
  • Zeng Xiaoming, Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of Alkynes. Angew Chem Int E 2010, 49, 942. <http://dx.doi.org/10.1002/anie.200905341>
  • Melaimi Mohand, Soleilhavoup Michèle, Bertrand Guy: Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes. Angew Chem Int Ed 2010, 49, 8810. <http://dx.doi.org/10.1002/anie.201000165>
  • Reznichenko Alexander L., Nguyen Hiep N., Hultzsch Kai C.: Asymmetric Intermolecular Hydroamination of Unactivated Alkenes with Simple Amines. Angew Chem Int Ed 2010, 49, 8984. <http://dx.doi.org/10.1002/anie.201004570>
  • Andrushko Natalia, Andrushko Vasyl, Roose Peter, Moonen Kristof, Börner Armin: Amination of Aliphatic Alcohols and Diols with an Iridium Pincer Catalyst. ChemCatChem 2010, 2, 640. <http://dx.doi.org/10.1002/cctc.201000046>
  • Hesp Kevin D., Stradiotto Mark: Rhodium- and Iridium-Catalyzed Hydroamination of Alkenes. ChemCatChem 2010, 2, 1192. <http://dx.doi.org/10.1002/cctc.201000102>
  • Tobisch Sven: Mechanistic Exploration of Intramolecular Aminodiene Hydroamination/Cyclisation Mediated by Constrained Geometry Organoactinide Complexes: A DFT Study. Chem Eur J 2010, 16, 3441. <http://dx.doi.org/10.1002/chem.200902356>
  • Tobisch Sven: Mechanistic Investigation of Organolanthanide-Mediated Hydroamination of Conjugated Aminodienes: A Comprehensive Computational Assessment of Various Routes for Diene Activation. Chem Eur J 2010, 16, 13814. <http://dx.doi.org/10.1002/chem.201001358>
  • Enthaler Stephan: Ammonia: An Environmentally Friendly Nitrogen Source for Primary Aniline Synthesis. ChemSusChem 2010, 3, 1024. <http://dx.doi.org/10.1002/cssc.201000145>
  • Biyikal Mustafa, Löhnwitz Karolin, Meyer Nils, Dochnahl Maximilian, Roesky Peter W., Blechert Siegfried: β-Diketiminate Zinc Complexes for the Hydroamination of Alkynes. Eur J Inorg Chem 2010, 2010, 1070. <http://dx.doi.org/10.1002/ejic.200900998>
  • Swapna Kokkirala, Murthy Sabbavarapu Narayana, Nageswar Yadavalli Venkata Durga: Copper Iodide as a Recyclable Catalyst for Buchwald N-Arylation. Eur J Org Chem 2010, 2010, 6678. <http://dx.doi.org/10.1002/ejoc.201000964>
  • Das Shoubhik, Zhou Shaolin, Addis Daniele, Enthaler Stephan, Junge Kathrin, Beller Matthias: Selective Catalytic Reductions of Amides and Nitriles to Amines. Top Catal 2010, 53, 979. <http://dx.doi.org/10.1007/s11244-010-9526-4>
  • Allan Laura E. N., Clarkson Guy J., Fox David J., Gott Andrew L., Scott Peter: Mechanism of Catalytic Cyclohydroamination by Zirconium Salicyloxazoline Complexes. J Am Chem Soc 2010, 132, 15308. <http://dx.doi.org/10.1021/ja106588m>
  • Hesp Kevin D., Tobisch Sven, Stradiotto Mark: [Ir(COD)Cl]2 as a Catalyst Precursor for the Intramolecular Hydroamination of Unactivated Alkenes with Primary Amines and Secondary Alkyl- or Arylamines: A Combined Catalytic, Mechanistic, and Computational Investigation. J Am Chem Soc 2010, 132, 413. <http://dx.doi.org/10.1021/ja908316n>
  • Qiu Shuifa, Xu Tao, Zhou Juan, Guo Yinlong, Liu Guosheng: Palladium-Catalyzed Intermolecular Aminofluorination of Styrenes. J Am Chem Soc 2010, 132, 2856. <http://dx.doi.org/10.1021/ja909716k>
  • Taylor Jason G., Adrio Luis A., Hii King Kuok (Mimi): Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?. Dalton Trans 2010, 39, 1171. <http://dx.doi.org/10.1039/b918970j>
  • Jovel Irina, Prateeptongkum Saisuree, Jackstell Ralf, Vogl Nadine, Weckbecker Christoph, Beller Matthias: α-Functionalization of non-activated aliphatic amines: ruthenium-catalyzed alkynylations and alkylations. Chem Commun 2010, 46, 1956. <http://dx.doi.org/10.1039/b924674f>
  • Pissarek Jens-Wolfgang, Schlesiger David, Roesky Peter W., Blechert Siegfried: Diethylzinc: A Simple and Efficient Catalyst for the Swift Hydroamination at Room Temperature. Adv Synth Catal 2009, 351, 2081. <http://dx.doi.org/10.1002/adsc.200900302>
  • Cui Xinjiang, Shi Feng, Tse Man Kin, Gördes Dirk, Thurow Kerstin, Beller Matthias, Deng Youquan: Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies. Adv Synth Catal 2009, 351, 2949. <http://dx.doi.org/10.1002/adsc.200900490>
  • Blank Benoît, Michlik Stefan, Kempe Rhett: Synthesis of Selectively Mono-N-Arylated Aliphatic Diamines via Iridium-Catalyzed Amine Alkylation. Adv Synth Catal 2009, 351, 2903. <http://dx.doi.org/10.1002/adsc.200900548>
  • Blank Benoît, Michlik Stefan, Kempe Rhett: Selective Iridium-Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions. Chem. Eur. J. 2009, 15, 3790. <http://dx.doi.org/10.1002/chem.200802318>
  • Qiu Shuifa, Wei Yunyang, Liu Guosheng: Palladium-Catalyzed Intramolecular Hydroamination of Allenes Coupled to Aerobic Alcohol Oxidation. Chem Eur J 2009, 15, 2751. <http://dx.doi.org/10.1002/chem.200802381>
  • Zeng Xiaoming, Frey Guido D., Kousar Shazia, Bertrand Guy: A Cationic Gold(I) Complex as a General Catalyst for the Intermolecular Hydroamination of Alkynes: Application to the One-Pot Synthesis of Allenes from Two Alkynes and a Sacrificial Amine. Chem Eur J 2009, 15, 3056. <http://dx.doi.org/10.1002/chem.200802626>
  • Reznichenko Alexander L., Hampel Frank, Hultzsch Kai C.: Kinetic Resolution of Aminoalkenes by Asymmetric Hydroamination: A Mechanistic Study. Chem Eur J 2009, 15, 12819. <http://dx.doi.org/10.1002/chem.200902229>
  • Lian Bing, Spaniol Thomas P., Horrillo-Martínez Patricia, Hultzsch Kai C., Okuda Jun: Imido and Amido Titanium Complexes that Contain a [OSSO]-Type Bis(phenolato) Ligand: Synthesis, Structures, and Hydroamination Catalysis. Eur J Inorg Chem 2009, 2009, 429. <http://dx.doi.org/10.1002/ejic.200800977>
  • Quinet Coralie, Sampoux Laetitia, Markó István E.: Base-Catalysed Intramolecular Hydroamination of Vinyl Sulfides. Eur J Org Chem 2009, 2009, 1806. <http://dx.doi.org/10.1002/ejoc.200900009>
  • Arundhathi Racha, Kantam Mannepalli Lakshmi, Prathima Parvathaneni Sai, Likhar Pravin R.: Amination of Alcohols Catalyzed by Copper-Aluminium Hydrotalcite: A Green Synthesis of Amines. Eur J Org Chem 2009, 2009, 5383. <http://dx.doi.org/10.1002/ejoc.200900628>
  • Delp Samuel A., Munro-Leighton Colleen, Khosla Chetna, Templeton Joseph L., Alsop Nikki M., Gunnoe T. Brent, Cundari Thomas R.: Combined experimental and computational study of W(II), Ru(II), Pt(IV) and Cu(I) amine and amido complexes using 15N NMR spectroscopy. J Organomet Chem 2009, 694, 1549. <http://dx.doi.org/10.1016/j.jorganchem.2009.01.006>
  • Aikawa Haruo, Tago Sakie, Umetsu Kazuteru, Haginiwa Naomichi, Asao Naoki: Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent. Tetrahedron 2009, 65, 1774. <http://dx.doi.org/10.1016/j.tet.2008.12.033>
  • Hultzsch Kai C., Horrillo-Martínez Patricia: Intramolecular hydroamination/cyclization of aminoalkenes catalyzed by diamidobinaphthyl magnesium- and zinc-complexes. Tetrahetron Lett 2009, 50, 2054. <http://dx.doi.org/10.1016/j.tetlet.2009.02.069>
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