Development of catalysts for the hydroamination of olefins

J. F. Hartwig

doi:10.1351/pac200476030507

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Valentine P. Ananikov, Sergey S. Zalesskiy, Vadim V. Kachala, and Irina P. Beletskaya

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Chae S. Yi

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Daniela V. Vitanova, Frank Hampel, and Kai C. Hultzsch

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Understanding the role of an easy-to-prepare aldimine–alkyne carboamination catalyst, [Ti(NMe2)3(NHMe2)][B(C6F5)4]

Falguni Basuli, Benjamin Wicker, John C. Huffman, and Daniel J. Mindiola

Journal of Organometallic Chemistry, 2011, Volume 696, Number 1, Page 235

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(+)-Neomenthyl- and (−)-phenylmenthyl-substituted cyclopentadienyl and indenyl yttrocenes as catalysts in asymmetric hydroamination/cyclization of aminoalkenes (AHA)

Daniela V. Vitanova, Frank Hampel, and Kai C. Hultzsch

Journal of Organometallic Chemistry, 2007, Volume 692, Number 21, Page 4690

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Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant

Tao Xu, Shuifa Qiu, and Guosheng Liu

Journal of Organometallic Chemistry, 2011, Volume 696, Number 1, Page 46

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Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine

Rei Kinjo, Bruno Donnadieu, and Guy Bertrand

Angewandte Chemie International Edition, 2011, Volume 50, Number 24, Page 5560

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Rei Kinjo, Bruno Donnadieu, and Guy Bertrand

Angewandte Chemie, 2011, Volume 123, Number 24, Page 5674

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Highly Efficient and Selective Catalytic N-Alkylation of Amines with Alcohols in Water

Jakob Norinder and Armin Börner

ChemCatChem, 2011, Volume 3, Number 9, Page 1407

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Priyabrata Das, David McLeod, and James McNulty

Tetrahedron Letters, 2011, Volume 52, Number 2, Page 199

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Cation exchange resin catalyzed hydroamination of vinylpyridines with aliphatic/aromatic amines

Mayur J. Bhanushali, Nitin S. Nandurkar, Malhari D. Bhor, and Bhalchandra M. Bhanage

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Mireia Rodriguez-Zubiri, Stephane Anguille, and Jean-Jacques Brunet

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Mechanism of Catalytic Cyclohydroamination by Zirconium Salicyloxazoline Complexes

Laura E. N. Allan, Guy J. Clarkson, David J. Fox, Andrew L. Gott, and Peter Scott

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Mechanistic investigation of organolanthanide-mediated hydroamination of aminoallenes: A comprehensive computational assessment of various routes for allene activation

Sven Tobisch

Dalton Trans., 2011, Volume 40, Number 1, Page 249

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Mechanistic Investigation of Organolanthanide-Mediated Hydroamination of Conjugated Aminodienes: A Comprehensive Computational Assessment of Various Routes for Diene Activation

Sven Tobisch

Chemistry - A European Journal, 2010, Volume 16, Number 46, Page 13814

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Copper Iodide as a Recyclable Catalyst for Buchwald N-Arylation

Kokkirala Swapna, Sabbavarapu Narayana Murthy, and Yadavalli Venkata Durga Nageswar

European Journal of Organic Chemistry, 2010, Volume 2010, Number 34, Page 6678

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Acid-Free Nickel Catalyst for Stereo- and Regioselective Hydrophosphorylation of Alkynes: Synthetic Procedure and Combined Experimental and Theoretical Mechanistic Study

Valentine P. Ananikov, Levon L. Khemchyan, Irina P. Beletskaya, and Zoya A. Starikova

Advanced Synthesis & Catalysis, 2010, Volume 352, Number 17, Page 2979

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Angewandte Chemie, 2010, Volume 122, Number 47, Page 9168

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Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes

Mohand Melaimi, Michèle Soleilhavoup, and Guy Bertrand

Angewandte Chemie International Edition, 2010, Volume 49, Number 47, Page 8810

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Asymmetric Intermolecular Hydroamination of Unactivated Alkenes with Simple Amines

Alexander L. Reznichenko, Hiep N. Nguyen, and Kai C. Hultzsch

Angewandte Chemie International Edition, 2010, Volume 49, Number 47, Page 8984

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Stabile cyclische Carbene und verwandte Spezies jenseits der Diaminocarbene

Mohand Melaimi, Michèle Soleilhavoup, and Guy Bertrand

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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

Weidong Rao, Prasath Kothandaraman, Chii Boon Koh, and Philip Wai Hong Chan

Advanced Synthesis & Catalysis, 2010, Volume 352, Number 14-15, Page 2521

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ChemCatChem, 2010, Volume 2, Number 10, Page 1192

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Chiral Neutral Zirconium Amidate Complexes for the Asymmetric Hydroamination of Alkenes

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Angewandte Chemie, 2006, Volume 119, Number 3, Page 358

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Angewandte Chemie International Edition, 2006, Volume 46, Number 3, Page 354

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[116]

Ammonia: An Environmentally Friendly Nitrogen Source for Primary Aniline Synthesis

Stephan Enthaler

ChemSusChem, 2010, Volume 3, Number 9, Page 1024

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Selective Catalytic Reductions of Amides and Nitriles to Amines

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Mechanistic Exploration of Intramolecular Aminodiene Hydroamination/Cyclisation Mediated by Constrained Geometry Organoactinide Complexes: A DFT Study

Sven Tobisch

Chemistry - A European Journal, 2010, Volume 16, Number 11, Page 3441

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α-Functionalization of non-activated aliphatic amines: ruthenium-catalyzed alkynylations and alkylations

Irina Jovel, Saisuree Prateeptongkum, Ralf Jackstell, Nadine Vogl, Christoph Weckbecker, and Matthias Beller

Chemical Communications, 2010, Volume 46, Number 11, Page 1956

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β-Diketiminate Zinc Complexes for the Hydroamination of Alkynes

Mustafa Biyikal, Karolin Löhnwitz, Nils Meyer, Maximilian Dochnahl, Peter W. Roesky, and Siegfried Blechert

European Journal of Inorganic Chemistry, 2010, Volume 2010, Number 7, Page 1070

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Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Jason G. Taylor, Luis A. Adrio, and King Kuok (Mimi) Hii

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Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of Alkynes

Xiaoming Zeng, Rei Kinjo, Bruno Donnadieu, and Guy Bertrand

Angewandte Chemie, 2010, Volume 122, Number 5, Page 954

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Synthesis of Selectively Mono-N-Arylated Aliphatic DiaminesviaIridium-Catalyzed Amine Alkylation

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Advanced Synthesis & Catalysis, 2009, Volume 351, Number 17, Page 2903

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Copper-CatalyzedN-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies

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Advanced Synthesis & Catalysis, 2009, Volume 351, Number 17, Page 2949

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Kinetic Resolution of Aminoalkenes by Asymmetric Hydroamination: A Mechanistic Study

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Chemistry - A European Journal, 2009, Volume 15, Number 46, Page 12819

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Amination of Alcohols Catalyzed by Copper-Aluminium Hydrotalcite: A Green Synthesis of Amines

Pravin R. Likhar, Racha Arundhathi, Mannepalli Lakshmi Kantam, and Parvathaneni Sai Prathima

European Journal of Organic Chemistry, 2009, Volume 2009, Number 31, Page 5383

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Diethylzinc: A Simple and Efficient Catalyst for the Swift Hydroamination at Room Temperature

Jens-Wolfgang Pissarek, David Schlesiger, Peter W. Roesky, and Siegfried Blechert

Advanced Synthesis & Catalysis, 2009, Volume 351, Number 13, Page 2081

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Hydroamination of conjugated dienes catalyzed by transition metal complexes

U. M. Dzhemilev, G. A. Tolstikov, and R. I. Khusnutdinov

Russian Journal of Organic Chemistry, 2009, Volume 45, Number 7, Page 957

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First iron-catalyzed synthesis of oximes from styrenes

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Dalton Transactions, 2009, Number 23, Page 4435

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Titanium hydroamination catalysts bearing a 2-aminopyrrolinato spectator ligand: monitoring the individual reaction steps

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Rhodium(I) and iridium(I) complexes containing bidentate phosphine-imidazolyl donor ligands as catalysts for the hydroamination and hydrothiolation of alkynes

Leslie D. Field, Barbara A. Messerle, Khuong Q. Vuong, and Peter Turner

Dalton Transactions, 2009, Number 18, Page 3599

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Selective Iridium-Catalyzed Alkylation of (Hetero)Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions

Benoît Blank, Stefan Michlik, and Rhett Kempe

Chemistry - A European Journal, 2009, Volume 15, Number 15, Page 3790

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[135]

Base-Catalysed Intramolecular Hydroamination of Vinyl Sulfides

Coralie Quinet, Laetitia Sampoux, and István E. Markó

European Journal of Organic Chemistry, 2009, Volume 2009, Number 11, Page 1806

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Palladium-Catalyzed Intramolecular Hydroamination of Allenes Coupled to Aerobic Alcohol Oxidation

Shuifa Qiu, Yunyang Wei, and Guosheng Liu

Chemistry - A European Journal, 2009, Volume 15, Number 12, Page 2751

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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

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Chemistry - A European Journal, 2009, Volume 15, Number 13, Page 3056

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Imido and Amido Titanium Complexes that Contain a [OSSO]-Type Bis(phenolato) Ligand: Synthesis, Structures, and Hydroamination Catalysis

Bing Lian, Thomas P. Spaniol, Patricia Horrillo-Martínez, Kai C. Hultzsch, and Jun Okuda

European Journal of Inorganic Chemistry, 2009, Volume 2009, Number 3, Page 429

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A General and Environmentally Benign Catalytic Reduction of Nitriles to Primary Amines

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Chemistry - A European Journal, 2008, Volume 14, Number 31, Page 9491

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A Selective and Practical Synthesis of Nitroolefins

Irina Jovel, Saisuree Prateeptongkum, Ralf Jackstell, Nadine Vogl, Christoph Weckbecker, and Matthias Beller

Advanced Synthesis & Catalysis, 2008, Volume 350, Number 16, Page 2493

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A Practical and Benign Synthesis of Primary Amines through Ruthenium-Catalyzed Reduction of Nitriles

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Sven Tobisch

Chemistry - A European Journal, 2008, Volume 14, Number 28, Page 8590

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Salt-Free Synthesis of Tertiary Amines by Ruthenium-Catalyzed Amination of Alcohols

Annegret Tillack, Dirk Hollmann, Kathleen Mevius, Dirk Michalik, Sebastian Bähn, and Matthias Beller

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Ruthenium-Catalyzed Synthesis of Secondary Alkylamines: Selective Alkylation with Aliphatic Amines

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Advanced Synthesis & Catalysis, 2008, Volume 350, Number 13, Page 2099

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Rare Earth and Alkaline Earth Metal Complexes with Me2Si-Bridged Cyclopentadienyl-Imidazolin-2-Imine Ligands and Their Use as Constrained-Geometry Hydroamination Catalysts

Tarun K. Panda, Cristian G. Hrib, Peter G. Jones, Jelena Jenter, Peter W. Roesky, and Matthias Tamm

European Journal of Inorganic Chemistry, 2008, Volume 2008, Number 27, Page 4270

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Palladium-Catalyzed Intermolecular Aerobic Oxidative Amination of Terminal Alkenes: Efficient Synthesis of Linear Allylamine Derivatives

Guosheng Liu, Guoyin Yin, and Liang Wu

Angewandte Chemie International Edition, 2008, Volume 47, Number 25, Page 4733

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Palladium-Catalyzed Intermolecular Aerobic Oxidative Amination of Terminal Alkenes: Efficient Synthesis of Linear Allylamine Derivatives

Guosheng Liu, Guoyin Yin, and Liang Wu

Angewandte Chemie, 2008, Volume 120, Number 25, Page 4811

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[148]

Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism

Xiaojuan Cheng, Yuanzhi Xia, Hua Wei, Bin Xu, Chongguang Zhang, Yahong Li, Guimin Qian, Xiaohua Zhang, Kai Li, and Wu Li

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Advanced Synthesis & Catalysis, 2008, Volume 350, Number 5, Page 749

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Catalytic alkene cyclohydroamination via an imido mechanism

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A Polymer-Bound Oxidovanadium(IV) Complex Prepared from anL-Cysteine-Derived Ligand for the Oxidative Amination of Styrene

Mannar R. Maurya, U. Kumar, Isabel Correia, Pedro Adão, and João Costa Pessoa

European Journal of Inorganic Chemistry, 2008, Volume 2008, Number 4, Page 577

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An Efficient Ceric Ammonium Nitrate-Catalyzed Aromatic Amination of (Ferrocenyl)(phenyl)methanol

Xiao-Ming SU and Shun-Jun JI

Chinese Journal of Chemistry, 2008, Volume 26, Number 1, Page 19

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Organolanthanide-Mediated Intermolecular Hydroamination of 1,3-Dienes: Mechanistic Insights from a Computational Exploration of Diverse Mechanistic Pathways for the Stereoselective Hydroamination of 1,3-Butadiene with a Primary Amine Supported by anansa-Neodymocene-Based Catalyst

Sven Tobisch

Chemistry - A European Journal, 2005, Volume 11, Number 21, Page 6372

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Gold-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines and Resulting High Chirality Transfer

Naoko Nishina and Yoshinori Yamamoto

Angewandte Chemie, 2006, Volume 118, Number 20, Page 3392

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Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt

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Chem. Commun., 2006, Number 21, Page 2221

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Naoko Nishina and Yoshinori Yamamoto

Angewandte Chemie International Edition, 2006, Volume 45, Number 20, Page 3314

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Hydroamidation of Alkenes withN-Substituted Formamides

Dilip Chandra Deb Nath, Christopher M. Fellows, Toshiaki Kobayashi, and Teruyuki Hayashi

Australian Journal of Chemistry, 2006, Volume 59, Number 3, Page 218

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[158]

Intramolecular hydroamination/cyclisation of aminoallenes mediated by a cationic zirconocene catalyst: a computational mechanistic study

Sven Tobisch

Dalton Transactions, 2006, Number 35, Page 4277

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Anti-Markovnikov hydroamination and hydrothiolation of electron-deficient vinylarenes catalyzed by well-defined monomeric copper(i) amido and thiolate complexes

Colleen Munro-Leighton, Samuel A. Delp, Nikki M. Alsop, Elizabeth D. Blue, and T. Brent Gunnoe

Chem. Commun., 2008, Number 1, Page 111

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Platinum-Catalyzed Intermolecular Hydroamination of Alkenes: Halide-Anion-Promoted Catalysis

Jean-Jacques Brunet, Ngoc-Chau Chu, and Mireia Rodriguez-Zubiri

European Journal of Inorganic Chemistry, 2007, Volume 2007, Number 30, Page 4711

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Exploring the Nickel-Catalyzed Oxidation of Alkenes: A Diamination by Sulfamide Transfer

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Angewandte Chemie International Edition, 2007, Volume 46, Number 37, Page 7125

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A Convenient and General Method for the Synthesis of Indole-2,3-dicarboxylates and 2-Arylindole-3-carboxylates

Iliyas Ali Sayyed, Karolin Alex, Annegret Tillack, Nicolle Schwarz, Dirk Michalik, and Matthias Beller

European Journal of Organic Chemistry, 2007, Volume 2007, Number 27, Page 4525

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Entwicklung Nickel-katalysierter Oxidationen von Alkenen: eine Diaminierung durch Sulfamid-Transfer

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Angewandte Chemie, 2007, Volume 119, Number 37, Page 7255

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Intramolecular Hydroamination with Homogeneous Zinc Catalysts: Evaluation of Substituent Effects inN,N′-Disubstituted Aminotroponiminate Zinc Complexes

Maximilian Dochnahl, Karolin Löhnwitz, Jens-Wolfgang Pissarek, Mustafa Biyikal, Sabrina R. Schulz, Sebastian Schön, Nils Meyer, Peter W. Roesky, and Siegfried Blechert

Chemistry - A European Journal, 2007, Volume 13, Number 23, Page 6654

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Structural variation, dynamics, and catalytic application of palladium(ii) complexes of di-N-heterocyclic carbene–amine ligands

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Dalton Trans., 2007, Number 28, Page 3065

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An Easy-To-Use, Regioselective, and Robust Bis(amidate) Titanium Hydroamination Precatalyst: Mechanistic and Synthetic Investigations toward the Preparation of Tetrahydroisoquinolines and Benzoquinolizine Alkaloids

Zhe Zhang, David C. Leitch, Man Lu, Brian O. Patrick, and Laurel L. Schafer

Chemistry - A European Journal, 2007, Volume 13, Number 7, Page 2012

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Syntheses of Four-Membered Metallacyclic Complexes with Nitrosylruthenium and Their Ring-Opening upon HCl Addition

Yasuhiro Arikawa, Kenta Ikeda, Taiki Asayama, Yoshimasa Nishimura, and Masayoshi Onishi

Chemistry - A European Journal, 2007, Volume 13, Number 14, Page 4024

DOI: 10.1002/chem.200601163

[168]

Base-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes – Scope, Limitations and Computational Studies

Patricia Horrillo-Martínez, Kai C. Hultzsch, Adrià Gil, and Vicenç Branchadell

European Journal of Organic Chemistry, 2007, Volume 2007, Number 20, Page 3311

DOI: 10.1002/ejoc.200700147

[169]

Elektrophile Aktivierung von Alkenen mit Platin(II): sehr viel mehr als eine langsame Variante von Palladium(II)

Anthony R. Chianese, Stephen J. Lee, and Michel R. Gagné

Angewandte Chemie, 2007, Volume 119, Number 22, Page 4118

DOI: 10.1002/ange.200603954

[170]

Intermolecular FeCl3-Catalyzed Hydroamination of Styrenes

Julien Michaux, Vincent Terrasson, Sylvain Marque, Johny Wehbe, Damien Prim, and Jean-Marc Campagne

European Journal of Organic Chemistry, 2007, Volume 2007, Number 16, Page 2601

DOI: 10.1002/ejoc.200700023

[171]

Electrophilic Activation of Alkenes by Platinum(II): So Much More Than a Slow Version of Palladium(II)

Anthony R. Chianese, Stephen J. Lee, and Michel R. Gagné

Angewandte Chemie International Edition, 2007, Volume 46, Number 22, Page 4042

DOI: 10.1002/anie.200603954

[172]

Intramolecular Hydroamination/Cyclisation of Aminoallenes Mediated by a Neutral Zirconocene Catalyst: A Computational Mechanistic Study

Sven Tobisch

Chemistry - A European Journal, 2007, Volume 13, Number 17, Page 4884

DOI: 10.1002/chem.200601287

[173]

Reactivity of Ruthenium(II) and Copper(I) Complexes that Possess Anionic Heteroatomic Ligands: Synthetic Exploitation of Nucleophilicity and Basicity of Amido, Hydroxo, Alkoxo, and Aryloxo Ligands for the Activation of Substrates that Possess Polar Bonds as well as Nonpolar C–H and H–H Bonds

T. Brent Gunnoe

European Journal of Inorganic Chemistry, 2007, Volume 2007, Number 9, Page 1185

DOI: 10.1002/ejic.200601072

[174]

An Improved Ruthenium Catalyst for the Environmentally Benign Amination of Primary and Secondary Alcohols

Dirk Hollmann, Annegret Tillack, Dirk Michalik, Ralf Jackstell, and Matthias Beller

Chemistry – An Asian Journal, 2007, Volume 2, Number 3, Page 403

DOI: 10.1002/asia.200600391

[175]

Asymmetric Catalytic Hydroamination of Activated Olefins in Ionic Liquids

Luca Fadini and Antonio Togni

Helvetica Chimica Acta, 2007, Volume 90, Number 2, Page 411

DOI: 10.1002/hlca.200790048

[176]

Eine allgemeine rutheniumkatalysierte Synthese von aromatischen Aminen

Dirk Hollmann, Sebastian Bähn, Annegret Tillack, and Matthias Beller

Angewandte Chemie, 2007, Volume 119, Number 43, Page 8440

DOI: 10.1002/ange.200703119

[177]

A General Ruthenium-Catalyzed Synthesis of Aromatic Amines

Dirk Hollmann, Sebastian Bähn, Annegret Tillack, and Matthias Beller

Angewandte Chemie International Edition, 2007, Volume 46, Number 43, Page 8291

DOI: 10.1002/anie.200703119

[178]

Origin of Diastereoselectivity in the Organolanthanide-Mediated Intramolecular Hydroamination/Cyclisation of Aminodienes: A Computational Exploration of Constrained Geometry CGC–Ln Catalysts

Sven Tobisch

Chemistry - A European Journal, 2007, Volume 13, Number 32, Page 9127

DOI: 10.1002/chem.200700616

[179]

Catalytic applications of transition-metal complexes bearing diphosphinidenecyclobutenes (DPCB)

Fumiyuki Ozawa and Masaaki Yoshifuji

Dalton Transactions, 2006, Number 42, Page 4987

DOI: 10.1039/b610327h

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