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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 4
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Original Articles

Facile Reduction of Azides with Sodium Borohydride/Copper (II) Sulphate System

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Pages 549-555 | Received 15 Jul 1993, Published online: 04 Jan 2007

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Read on this site (5)

D. Amantini, F. Fringuelli, F. Pizza & L. Vaccaro. (2002) SELECTED METHODS FOR THE REDUCTION OF THE AZIDO GROUP. Organic Preparations and Procedures International 34:2, pages 109-147.
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PierLucio Anelli, Luciano Lattuada & Fulvio Uggeri. (1998) One-Pot Mitsunobu-Staudinger Preparation of 3-Aminocholan-24-oic Acid Esters from 3-Hydroxycholan-24-oic Acid Esters. Synthetic Communications 28:1, pages 109-117.
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You Huang, Yongmin Zhang & Yulu Wang. (1996) Reduction of Azides to Amines With SmI2 or Cp2TiCl2-Sm System. Synthetic Communications 26:15, pages 2911-2915.
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Christina Tzitzoglaki, Antonios Drakopoulos, Athina Konstantinidi, Ioannis Stylianakis, Marianna Stampolaki & Antonios Kolocouris. (2019) Approaches to primary tert-alkyl amines as building blocks. Tetrahedron 75:34, pages 130408.
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Benan Kilbas, Yunus Emre Yilmaz & Sinem Ergen. (2018) A practical and highly efficient transfer hydrogenation of aryl azides using a [Ru(p-cymene)Cl2]2 catalyst and sodium borohydride. Comptes Rendus. Chimie 21:9, pages 880-883.
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Niankai Fu, Gregory S. Sauer, Ambarneil Saha, Aaron Loo & Song Lin. (2017) Metal-catalyzed electrochemical diazidation of alkenes. Science 357:6351, pages 575-579.
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Elodie Lohou, N. André Sasaki, Agnès Boullier & Pascal Sonnet. (2016) Multifunctional diamine AGE/ALE inhibitors with potential therapeutical properties against Alzheimer's disease. European Journal of Medicinal Chemistry 122, pages 702-722.
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Noriyoshi Arai, Nozomi Onodera & Takeshi Ohkuma. (2016) Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports. Tetrahedron Letters 57:37, pages 4183-4186.
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Robert V. Hoffman, H. Surya Prakash Rao, Shaik Rafi, Martin Pichette Drapeau & Thierry Ollevier. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 11 .
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Aarón Flores-Figueroa, Oliver Kaufhold, Kai-Oliver Feldmann & F. Ekkehardt Hahn. (2009) Synthesis of NHC complexes by template controlled cyclization of β-functionalized isocyanides. Dalton Transactions:42, pages 9334.
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Jérôme Waser, Boris Gaspar, Hisanori Nambu & Erick M. Carreira. (2006) Hydrazines and Azides via the Metal-Catalyzed Hydrohydrazination and Hydroazidation of Olefins. Journal of the American Chemical Society 128:35, pages 11693-11712.
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Yuhong Ju, Dalip Kumar & Rajender S. Varma. (2006) Revisiting Nucleophilic Substitution Reactions:  Microwave-Assisted Synthesis of Azides, Thiocyanates, and Sulfones in an Aqueous Medium. The Journal of Organic Chemistry 71:17, pages 6697-6700.
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Ahmed Kamal, N. Shankaraiah, K. Laxma Reddy & V. Devaiah. (2006) Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81. Tetrahedron Letters 47:25, pages 4253-4257.
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Peng‐Wu Zheng, Xue‐Min Xie, Wei Wang, Xiao‐Ji Wang, Yu‐Ping Guo & Qi‐Dong Tu. (2006) Reduction of Azide to Amine Using Fe/AlCl 3 or Fe/BiCl 3 System in Aqueous EtOH . Chinese Journal of Chemistry 24:6, pages 825-826.
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Stefan Bräse, Carmen Gil, Kerstin Knepper & Viktor Zimmermann. (2005) Organic Azides: An Exploding Diversity of a Unique Class of Compounds. Angewandte Chemie International Edition 44:33, pages 5188-5240.
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Stefan Bräse, Carmen Gil, Kerstin Knepper & Viktor Zimmermann. (2005) Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse. Angewandte Chemie 117:33, pages 5320-5374.
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Jérôme Waser, Hisanori Nambu & Erick M. Carreira. (2005) Cobalt-Catalyzed Hydroazidation of Olefins: Convenient Access to Alkyl Azides. Journal of the American Chemical Society 127:23, pages 8294-8295.
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Michael P. Cassidy, Ayse Daut Özdemir & Albert Padwa. (2005) An Aza-Wittig/π-Furan Cyclization Approach Toward the Homoerythrina Alkaloid (±)-Selaginoidine. Organic Letters 7:7, pages 1339-1342.
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Stephan Bedürftig & Bernhard Wünsch. (2004) Chiral, nonracemic (piperazin-2-yl)methanol derivatives with σ-receptor affinity. Bioorganic & Medicinal Chemistry 12:12, pages 3299-3311.
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Ahmed Kamal, K.Venkata Ramana, Hari Babu Ankati & A.Venkata Ramana. (2002) Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones. Tetrahedron Letters 43:38, pages 6861-6863.
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Ahmed Kamal, P.S.M.M. Reddy & D.Rajasekhar Reddy. (2002) Simple and facile reduction of azides to amines: synthesis of DNA interactive pyrrolo[2,1- c ][1,4]benzodiazepines. Tetrahedron Letters 43:37, pages 6629-6631.
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X.Eric Hu, Nick K Kim, Benoit Ledoussal & Anny-Odile Colson. (2002) Regio- and stereo-controlled copper organometallic addition to a piperidinyl aziridine: synthesis of trans 3-amino-4-alkyl-piperidines. Tetrahedron Letters 43:23, pages 4289-4293.
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Sergei V. Chapyshev & Matthew S. Platz. (2001) Selective reduction of the azido groups of 2,4,6-triazidopyridines. Mendeleev Communications 11:2, pages 56-57.
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Ahmed Kamal, E Laxman & M Arifuddin. (2000) An efficient reduction of azides to amines: synthesis of DNA interactive pyrrolo[2,1-c][1,4]benzodiazepines. Tetrahedron Letters 41:40, pages 7743-7746.
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Mariappan Periasamy & Muniappan Thirumalaikumar. (2000) Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis. Journal of Organometallic Chemistry 609:1-2, pages 137-151.
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Corrado Malanga, Serena Mannucci & Luciano Lardicci. (2019) Nickel Mediated Reduction of Azides by Bu 3 Snh . Journal of Chemical Research 2000:6, pages 256-257.
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Imma Bosch, Anna M. Costa, Manuel Martín, Fèlix Urpí & Jaume Vilarrasa. (2000) Reduction of Azides to Amines Mediated by Tin Bis(1,2-benzenedithiolate). Organic Letters 2:3, pages 397-399.
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Habib Firouzabadi & Gholam Reza Afsharifar. (1995) Modified Borohydride Agents, 1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane Tetrahydroborate (BAAOTB) versus Tetrabutylammonium Tetrahydroborate (TBATB). Efficient, Selective, and Versatile Reducing Agents. Bulletin of the Chemical Society of Japan 68:9, pages 2595-2602.
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