* Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE).This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl 2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH 2] + Cl −) with water (H 2 O). Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication This article is part of the themed collection: For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. The reaction is known as Stephen’s Reduction. For esters and nitriles, LiAlH4 is modified into the organometallic reagent diisobutyl aluminum hydride which can be represented as DIBAL or DIBAL-H or DIBAH or DIBALH. Herein we report the reduction of aromatic nitriles into aldehydes with calcium hypophosphite in the presence of base and nickel(II) complex in a water/ethanol mixture.This catalytic system reduced efficiently a series of aromatic nitriles bearing different functional groups such as –Cl, –CF 3, –Br, –CH 3, –OCH 3, –COOCH 2 CH 3, –OH and –CHO. This may take some time to load. Fetching data from CrossRef. Commonly quoted catalysts are palladium, platinum or nickel. https://doi.org/10.1016/S0040-4039(02)00027-8. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. ahachem@ul.edu.lb XX is the XXth reference in the list of references. It will reduce aldehydes, ketones, esters, carboxylic acid chlorides, carboxylic acids and even carboxylate salts to alcohols. Please enable JavaScript This mild method may be generally applied to multi-step organic synthesis. The reduction of nitriles using hydrogen and a metal catalyst. Carboxylic acids can be converted to acid chlorides using thionyl chloride which can then be reduced to aldehydes using LiAlH(O-t-Bu)3. to access the full features of the site or access our. Go to our The nitrile is then reduced by the transfer of a hydride ion to the carbon of the carbon-nitrile triple bond, producing an imine. This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. Tel: +96-1-3-31-95-49. The carbon-nitrogen triple bond in a nitrile can also be reduced by reaction with hydrogen gas in the presence of a variety of metal catalysts. In all cases the Ref. it in a third party non-RSC publication you must Reduction of nitriles with the compound Stannous Chloride (SnCl 2) in the presence of HCl leads to the formation of the nitrile compound’s corresponding imine form. You do not have JavaScript enabled. is available on our Permission Requests page. E-mail: Following are the structures for these compounds: If you are not the author of this article and you wish to reproduce material from Authors contributing to RSC publications (journal articles, books or book chapters) In each case the partially negative hydrogen reacts with the partially positive carbon of the substrate. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Watch the recordings here on Youtube! Laboratoire de Catalyse, Synthèse et Environnement, Institute de Chimie et Biochimie Moléculaires et Supramoléculaire (ICBMS), CNRS, UMR 5246, Université Claude Bernard Lyon 1, Campus de la Doua, 43 boulevard du 11 Novembre 1918, bâtiment Curien-CPE, 69622 Villeurbanne cedex, France The reduction of esters, acid chlorides, and nitriles require reducing agents that are derivatives of lithium aluminum hydride (LiAlH4). or in a thesis or dissertation provided that the correct acknowledgement is given R. Mouselmani, A. Hachem, A. Alaaeddine, E. Métay and M. Lemaire, Laboratoire de Catalyse, Synthèse et Environnement, Institute de Chimie et Biochimie Moléculaires et Supramoléculaire (ICBMS), CNRS, UMR 5246, Université Claude Bernard Lyon 1, Campus de la Doua, 43 boulevard du 11 Novembre 1918, bâtiment Curien-CPE, 69622 Villeurbanne cedex, France, Laboratoire de Chimie Médicinale et des Produits Naturels, Université Libanaise, Campus Universitaire Rafic Hariri Hadath, Faculte des Sciences, 4eme étage, Beirut, Lebanon, Instructions for using Copyright Clearance Center page. The reducing agents of choice are usually lithium tri‐tert‐butoxy aluminum hydride (LATB—H) and diisobutylaluminum hydride (DIBAL—H). with the reproduced material. During the synthesis, ammonium chloride is also produced. By continuing you agree to the use of cookies. … 19.4 New Synthesis of Aldehydes and Ketones, Organocuprate reagents react with Acid Chlorides to form Ketones, 19.3: Review of Ketone and Aldehyde Synthesis, 19.5: Nucleophilic Addition Reactions of Ketones and Aldehydes, Ester, Acid Chloride, and Nitrile Reduction to form Aldehydes, Carboxylic Acids can be converted to Aldehydes, Grignard reagents react with Nitriles to form Ketones. The reduction of esters, acid chlorides, and nitriles require reducing agents that are derivatives of lithium aluminum hydride (LiAlH 4).For esters and nitriles, LiAlH 4 is modified into the organometallic reagent diisobutyl aluminum hydride which can be represented as DIBAL or DIBAL-H or DIBAH or DIBALH. To reduce acid chlorides, t-butoxide groups are combined with LiAlH4 to form lithium tritert-butoxy aluminum hydride.