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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 20
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Original Articles

A Facile One-Pot Conversion of Aldehydes into Nitriles

Samuel T. Chill Department of Chemistry, University of Tennessee at Chattanooga, Chattanooga, Tennessee, USA
&
Robert C. Mebane Department of Chemistry, University of Tennessee at Chattanooga, Chattanooga, Tennessee, USACorrespondence[email protected]
Pages 3601-3606 | Received 17 Nov 2008, Published online: 08 Sep 2009

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VirgilioP. Gozum & RobertC. Mebane. (2013) Solvent-free and atom efficient conversion of aldehydes into nitriles. Green Chemistry Letters and Reviews 6:2, pages 149-150.
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PatrickJ. Siler, SamuelT. Chill & RobertC. Mebane. (2011) Tandem One-Pot Conversion of Aldehydes into Ethyl Esters. Synthetic Communications 41:8, pages 1247-1250.
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SamuelT. Chill & RobertC. Mebane. (2010) Facile One-Pot Conversion of Aldehydes into Amides. Synthetic Communications 40:13, pages 2014-2017.
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Articles from other publishers (34)

Anastasia A. Smorodina, Evgeny M. Buev, Vladimir S. Moshkin & Vyacheslav Y. Sosnovskikh. (2023) Arylethanolamines in Ritter reaction: Synthesis of 2,4‐Diarylimidazole Core. Asian Journal of Organic Chemistry 12:2.
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Yin Wang, Xuetong Wang, Yanwu Li, Xiuyu Zhang, Lingli Li, Tingshu He, Jianyong Yuan & Suqin Shang. (2022) Imidazole Hydrochloride Promoted Synthesis of Nitriles from Aldehydes. Current Organic Synthesis 19:8, pages 923-929.
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Maryam Bigdelo, Firouzeh Nemati & Yalda Rangraz. (2022) Organoselenium functionalized SBA-15 as a new catalyst for the cyanide-free conversion of oximes to nitriles. BMC Chemistry 16:1.
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Hayedeh Gorjian & Nader Ghaffari Khaligh. (2022) Ball-Milling Technique for the Straightforward Synthesis of Nitriles from Aldehydes Using Poly( N -vinylimidazole): Is the Mechanochemical Procedure a Practical Metal- and Solvent-Free Synthetic Method? . ACS Sustainable Chemistry & Engineering 10:32, pages 10457-10464.
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Jannis Nonnhoff & Harald Gröger. (2021) Process Development of the Copper(II)‐Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co‐Substrate. ChemistryOpen 11:1.
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Mohamed H. El-Shershaby, Kamal M. El-Gamal, Ashraf H. Bayoumi, Khaled El-Adl, Mohamed Alswah, Hany E. A. Ahmed, Ahmed A. Al-Karmalamy & Hamada S. Abulkhair. (2021) The antimicrobial potential and pharmacokinetic profiles of novel quinoline-based scaffolds: synthesis and in silico mechanistic studies as dual DNA gyrase and DHFR inhibitors . New Journal of Chemistry 45:31, pages 13986-14004.
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Hongyan Lin, Ziling Zhou, Xiaopeng Ma, Qingqing Chen, Hongwei Han, Xiaoming Wang, Jinliang Qi & Yonghua Yang. (2021) One pot synthesis of aryl nitriles from aromatic aldehydes in a water environment. RSC Advances 11:39, pages 24232-24237.
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N. Uludag. (2020) An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions. Russian Journal of Organic Chemistry 56:9, pages 1640-1645.
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Yelizaveta Gorbunova, Dmitriy N. Zakusilo, Irina A. Boyarskaya & Aleksander V. Vasilyev. (2020) Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones. Tetrahedron 76:26, pages 131264.
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P. L. Pujari, P. V. Thorat, A. B. Mahipal & R. S. Bhondwe. (2019) Highly Efficient Microwave-assisted One-Pot Synthesis of Aromatic Nitriles from Aromatic Aldehydes. Russian Journal of Organic Chemistry 55:5, pages 702-706.
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Thatikonda Narendar Reddy, Adilson Beatriz, Vaidya Jayathirtha Rao & Dênis Pires de Lima. (2019) Carbonyl Compounds′ Journey to Amide Bond Formation. Chemistry – An Asian Journal 14:3, pages 344-388.
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Boris Guicheret, Yann Bertholo, Philippe Blach, Yann Raoul, Estelle Métay & Marc Lemaire. (2018) A Two‐Step Oxidative Cleavage of 1,2‐Diol Fatty Esters into Acids or Nitriles by a Dehydrogenation–Oxidative Cleavage Sequence. ChemSusChem 11:19, pages 3431-3437.
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Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 85 .
Xiaoyun Ma, Jun Ao, Zhengjian Chen & Yi Liu. (2017) Copper (II)-catalysed direct conversion of aldehydes into nitriles in acetonitrile. Journal of Chemical Research 41:8, pages 465-468.
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Antonella Leggio, Emilia Lucia Belsito, Sonia Gallo & Angelo Liguori. (2017) One-pot conversion of aldehydes to nitriles mediated by TiCl 4. Tetrahedron Letters 58:15, pages 1512-1514.
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Suraj K. Pathak, Monika Gupta, Santanu K. Pal & Ammathnadu S. Achalkumar. (2016) Hexacatenars Exhibiting π-π Driven Supergelation, Aggregation Induced Blue Light Emission and Thermochromism. ChemistrySelect 1:16, pages 5107-5120.
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Hashim Motiwala, Qin Yin & Jeffrey Aubé. (2015) Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol. Molecules 21:1, pages 45.
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Markus Laube, Cemena Gassner, Sai Kiran Sharma, Robert Günther, Arne Pigorsch, Jonas König, Martin Köckerling, Frank Wuest, Jens Pietzsch & Torsten Kniess. (2015) Diaryl-Substituted (Dihydro)pyrrolo[3,2,1- hi ]indoles, a Class of Potent COX-2 Inhibitors with Tricyclic Core Structure . The Journal of Organic Chemistry 80:11, pages 5611-5624.
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Qinghui Qu, Xiaofang Gao, Jian Gao & Gaoqing Yuan. (2015) A highly efficient electrochemical route for the conversion of aldehydes to nitriles. Science China Chemistry 58:4, pages 747-750.
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Nail M. Shavaleev & Svetlana V. Eliseeva. (2015) Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands. Inorganica Chimica Acta 427, pages 81-86.
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Pascale Crochet & Victorio Cadierno. (2015) Catalytic synthesis of amides via aldoximes rearrangement. Chemical Communications 51:13, pages 2495-2505.
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Nail M. Shavaleev, Svetlana V. Eliseeva, Rosario Scopelliti & Jean-Claude G. Bünzli. (2014) Tridentate Benzimidazole-Pyridine-Tetrazolates as Sensitizers of Europium Luminescence. Inorganic Chemistry 53:10, pages 5171-5178.
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Daniel Conole, Thorsten M. Beck, Morgan Jay-Smith, Malcolm D. Tingle, Charles T. Eason, Margaret A. Brimble & David Rennison. (2014) Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides. Bioorganic & Medicinal Chemistry 22:7, pages 2220-2235.
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Li Wang, Xiaojie Zhang, Jidong Zhang, Hongkun Tian, Yunfeng Lu, Yanhou Geng & Fosong Wang. (2014) Synthesis and characterization of oligo(2,5-bis(3-dodecylthiophen-2-yl)thieno[3,2-b]thiophene)s: effect of the chain length and end-groups on their optical and charge transport properties. J. Mater. Chem. C 2:46, pages 9978-9986.
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靓 吴. (2013) Recent Research Advances on the Conversion of Aromatic Aldehydes into Aromatic Nitriles. Journal of Organic Chemistry Research 01:02, pages 3-8.
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A. Ebru Aydin & Seda Yuksekdanaci. (2013) Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands. Tetrahedron: Asymmetry 24:1, pages 14-22.
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Maryam Hajjami, Arash Ghorbani-Choghamarani, Mohammad Ali Zolfigol & Fatemeh Gholamian. (2012) An efficient and versatile synthesis of aromatic nitriles from aldehydes. Chinese Chemical Letters 23:12, pages 1323-1326.
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Nemai C. Ganguly, Sushmita Roy & Pallab Mondal. (2012) An efficient copper(II)-catalyzed direct access to primary amides from aldehydes under neat conditions. Tetrahedron Letters 53:11, pages 1413-1416.
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Mohammad Ali Zolfigol, Maryam Hajjami & Arash Ghorbani-Choghamarani. (2011) A Simple and One-pot Oxidative Conversion of Alcohols or Aldehydes to the Nitriles using NaIO 4 /KI in Aqueous NH 3 . Bulletin of the Korean Chemical Society 32:12, pages 4191-4194.
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Helen C. Aspinall, Oliver Beckingham, Michael D. Farrar, Nicholas Greeves & Christopher D. Thomas. (2011) A general and convenient route to oxazolyl ligands. Tetrahedron Letters 52:40, pages 5120-5123.
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Samuel T. Chill & Robert C. Mebane. (2010) ChemInform Abstract: A Facile One‐Pot Conversion of Aldehydes into Nitriles.. ChemInform 41:13.
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