1127-1130. 0000019572 00000 n It is only powerful enough to reduce aldehydes, ketones and acid chlorides to alcohols: esters, amides, acids and nitriles are largely untouched. In a typical procedure, in a 100 ml conical flask mounted over a magnetic stirrer, fitted with reflux condenser and a mercury trap, was placed a mixture of nitrile (9.8 mmol), The focus has shifted more recently to its applications as a reducing You have to login with your ACS ID befor you can login with your Mendeley account. https://doi.org/10.1021/bk-2013-1128.ch010. It desulfurizes these compounds unfortunately. These metrics are regularly updated to reflect usage leading up to the last few days. NiCl26H2O (Qualigens) was used after drying in a nickel crucible in an 0000008651 00000 n 0000005515 00000 n It can also behave as a nucleophile toward halides and epoxides. 0000044844 00000 n Soc. amines. 0000016706 00000 n 0000019921 00000 n Nickel boride loses its activity with time since benzonitrile (1a) 0000010993 00000 n Your Mendeley pairing has expired. [10a-b], The products isolated are p-aminobenzylamine and di(p-aminobenzyl)amine. by a simple work-up procedure. 0000005751 00000 n The reduction of a nitrile (CN) group by sodium borohydride: The preparation of phosphineamine and phosphine-imidate complexes of tungsten carbonyl. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. is the nitrile moiety. 0000006577 00000 n Reduction of nitriles to primary amines with LiAlH4. 0000009632 00000 n New comments cannot be posted and votes cannot be cast, A community for chemists and those who love chemistry, Press J to jump to the feed. In the sodium borohydride reduction the methanol solvent system achieves this hydrolysis automatically. [7] have %PDF-1.3 %���� Chem. 0000004037 00000 n We report herein a simple and convenient procedure for the reduction of the robust cyano group in aromatic nitriles 1 to primary amines 2 directly in high yields with nickel There are a variety of known methodologies to reduce nitriles, including using lithium aluminum hydride, catalytic hydrogénation, and borane*dimethylsulfide (Smith and March 2001). Chem. Esters such as methyl, ethyl, tert-butyl, and It is noteworthy that the toxicity of this procedure is greatly reduced due to its catalytic nature in nickel(II) chloride used in combination with excess sodium borohydride. filtered through a celite pad after ~15 min. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. In acidic aqueous solutions, only one N-CH2CH2NH2 group of [NiL2]2+ was protonated selectively to yield [Ni(HL2)]3+, which is inert to protonation.Download : Download high-res image (50KB)Download : Download full-size image. 0000006695 00000 n Sodium Borohydride Barton Deoxygenation Reduction of Alkyl Tosylates Diazene-Mediated Deoxygenation 0000010194 00000 n The filtered nickel boride precipitate was washed with ethanol (2×10 ml). A nickel boride catalyzed reduction of nitriles allows the preparation of Boc protected amines. 1986, 86, 763; Itsuno, S.; Sakurai, Y.; Ito, K. Synthesis 1988, 995; Satoh, T.; Nishiki, M.; Miyataka, H.; Niino, Y.; Mitsuo, N. Tetrahedron Lett. Sodium borohydride is a milder reducing agent than lithium aluminium hydride (LAH), is comparatively inexpensive, easier to handle and can also be employed in protic 0000002808 00000 n 6. 0000033978 00000 n nickel boride in methanol at ambient temperature to give the parent carboxylic Find more information about Crossref citation counts. 1972, 37, 3552. Reduction to amines [LiAlH 4 ] Explained: Treatment of nitriles with a strong hydride reducing agents such as lithium aluminum hydride results in double hydride addition, giving primary amine on aqueous workup. 1998, 39, 3829; Szendi, Z.; Dombi, G.; Vincze, I. Monatsh. Rev. 0000004579 00000 n 0000003579 00000 n Journal of Chemical Education 2005, 82 (11) , 1674. trailer << /Size 314 /Info 230 0 R /Root 233 0 R /Prev 197788 /ID[] >> startxref 0 %%EOF 233 0 obj << /Type /Catalog /Pages 231 0 R /Outlines 236 0 R /Names 234 0 R /OpenAction [ 235 0 R /FitH 803 ] /PageMode /UseOutlines >> endobj 234 0 obj << /Dests 229 0 R >> endobj 312 0 obj << /S 363 /T 551 /O 601 /E 617 /Filter /FlateDecode /Length 313 0 R >> stream 6. boride at ambient temperature. Copyright © 2016 Elsevier B.V. All rights reserved. [10a-b]. & Proced. Commun., in press. Nitriles 1a, 1b and 1r were obtained from commercial sources and were The Discovery-Oriented Approach to Organic Chemistry. This file is a part of the Rhodium site archive. Haridwar, India, Nov. 2000, Handbook, pp. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride. 0000022827 00000 n The formation of secondary amines could not be eliminated completely despite attempting reactions 232 0 obj << /Linearized 1 /O 235 /H [ 2183 647 ] /L 202558 /E 46043 /N 7 /T 197799 >> endobj xref 232 82 0000000016 00000 n