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0000005669 00000 n 0000004060 00000 n [1], Borane-tetrahydrofuran (BH3-THF) reduction of nitriles is typically performed in THF with heating. 0000002266 00000 n Lithium Aluminum Hydride is a powerful hydride donor that reacts rapidly with nitriles to produce amines. <<07b6cbcfb320354f8ff6148750fce7ec>]>> [1] 1) Carey, F. A.; Sundberg, R. J.; Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th Edition, 2) Caron, S.; Practical Synthetic Organic Chemistry, 3) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents, 4) Anderson, N. G.; Practical Process Research and Development, a Guide for Organic Chemists, 2nd Edition, 5) Smith, M. B.; March's Advanced Organic Chemistry, 7th Edition. 0000001228 00000 n BH3-SMe2 is more stable than BH3-THF and is available in much higher concentrations (10 M). 0000011214 00000 n The use of (Xantphos)CoCl2 and ammonia borane (NH3−BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH−BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user‐friendly cobalt complex, (Xantphos)CoCl2, is reported. 0000010360 00000 n During this reaction the hydride nucleophile attacks the electrophilic carbon in the nitrile to form an imine anion. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. 0000000854 00000 n %PDF-1.4 %���� 1504 0 obj <> endobj trailer Activated samarium diiodide features excellent functional group tolerance and is therefore an attractive alternative to pyrophoric alkali metal hydrides. A Theoretical Investigation of Iron-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines. and you may need to create a new Wiley Online Library account. The use of (Xantphos)CoCl 2 and ammonia borane (NH 3 −BH 3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl 2 and dimethylamine borane (Me 2 NH−BH 3) along with external amines produce unsymmetrical secondary amines and tertiary amines. 3 0000005926 00000 n Working off-campus? [2][3], Catalytic hydrogenation of nitriles can form secondary and tertiary amine by-pdts. Despite its name, the structure of the reducing agent is very simple. 0000014661 00000 n 0000004301 00000 n The dianion can then be converted to an amine by addition of water. O Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, By continuing to browse this site, you agree to its use of cookies as described in our, I have read and accept the Wiley Online Library Terms and Conditions of Use. The reducing agent. 0000002294 00000 n Ammonia borane as a reducing agent in organic synthesis. 0000006649 00000 n 0000005197 00000 n 0000003813 00000 n 1504 27 If you do not receive an email within 10 minutes, your email address may not be registered,

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