The carbonyl group is most commonly a ketone or an aldehyde. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Use the link below to share a full-text version of this article with your friends and colleagues. Electrophilic [N-F] Aldehydes and ketones can be converted into 1 o, 2 o and 3 o amines using reductive amination. Get article recommendations from ACS based on references in your Mendeley library. N Worth Publishing: New York, 2000. See this image and copyright information in PMC. A classic named reaction is the Mignonac reaction (1921) involving reaction of a ketone with ammonia over a nickel catalyst for example in a synthesis of 1-phenylethylamine starting from acetophenone:, Nowadays, one-pot reductive amination fulfil by acid-metal catalysts that act as a hydride transfer. + Remote Organic Chemistry Laboratories at University of Michigan—Dearborn. Environmental Catalysis (WILEY‐VCH, 2008). In a 1000ml wide-mouthed Erlenmeyer flask, 19 grams of aluminum foil cut to 3x3cm pieces was amalgamated in a solution of 500mg mercuric … Q. P. B. Nguyen, T. H. Kim, Synthesis… Learn about our remote access options, Department of Chemistry, University of Basel, St. Johanns‐Ring 19, 4056 Basel, Switzerland, Department of Chemistry, University of Basel, Mattenstrasse 24a, 4002 Basel, Switzerland. | 2010 Nov;39(11):4130-45. doi: 10.1039/c003692g. The entire sequence is performed in an open beaker in less than one hour. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. These hydride reagents also must tolerate moderately acidic conditions. Chem Soc Rev. The reductive amination (RA) reaction plays a pivotal role in the synthesis of new C–N bonds, due to the availability of many different and low‐cost reagents and their operational simplicity. This method is sometimes called indirect reductive amination. One-Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “on Water”. Senthamarai T, Murugesan K, Schneidewind J, Kalevaru NV, Baumann W, Neumann H, Kamer PCJ, Beller M, Jagadeesh RV. Please reconnect. Epub 2010 Sep 28. Reductive Amination in the Synthesis of Pharmaceuticals. 2019 Apr 1;58(15):5064-5068. doi: 10.1002/anie.201812100. For more information contact us at email@example.com or check out our status page at https://status.libretexts.org. Independent Synthesis Projects in the Organic Chemistry Teaching Laboratories: Bridging the Gap Between Student and Researcher. http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1021/acs.jchemed.0c00812, https://doi.org/10.1021/bk-2020-1345.ch010, https://doi.org/10.1021/bk-2019-1312.ch011, https://doi.org/10.1021/acs.jchemed.7b00458, https://doi.org/10.1021/acs.jchemed.7b00093, https://doi.org/10.1021/acs.jchemed.5b00815, https://doi.org/10.1021/acs.jchemed.6b00056, https://doi.org/10.1021/bk-2009-1011.ch002, https://doi.org/10.1016/j.ijms.2012.12.004, https://doi.org/10.1080/00397910903370725, https://doi.org/10.1080/17518250903164549.
Last edited on 12 November 2020, at 19:35, "Nouvelle méthode générale de préparation des amines à partir des aldéhydes ou des cétones", https://en.wikipedia.org/w/index.php?title=Reductive_amination&oldid=988370533, Creative Commons Attribution-ShareAlike License, This page was last edited on 12 November 2020, at 19:35. The excitation of a RuII photosensitizer in the presence of ascorbic acid leads to the reduction of iminium ions to electron‐rich α‐aminoalkyl radical intermediates, which are rapidly converted into reductive amination products by thiol‐mediated hydrogen atom transfer (HAT). ,1-diphenylmethanimine. A reducing agent commonly used for this reaction is sodium cyanoborohydride (NaBH3CN). The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.The first step is a spectacular solvent-free solid-solid reaction between ortho-vanillin and para-toluidine to synthesize an imine in quantitative yield. If you do not receive an email within 10 minutes, your email address may not be registered, Learn more. If you have previously obtained access with your personal account, please log in. Electronic Supporting Information files are available without a subscription to ACS Web Editions. How the Principles of Green Chemistry Changed the Way Organic Chemistry Labs Are Taught at the University of Detroit Mercy.
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