It is recommended that BH3-THF is used below 35 C (for safety). 0000003813 00000 n One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt–Fe Use the link below to share a full-text version of this article with your friends and colleagues. 0000001437 00000 n 1506 0 obj<>stream The full text of this article hosted at iucr.org is unavailable due to technical difficulties. . 0000004425 00000 n

Nitrile hydrogenation is an important method to obtain amines. Decomposition of BH3-THF can generate H2 and tributyl borate. x�b```b``�c`e`���ˀ �@16�@��N��_��)�ٗ��C�L�qY. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. xref startxref [2][3][4], Borane-dimethylsulfide (BH3-SMe2) reduction of nitriles is typically performed in THF with heating. Lithium Aluminum Hydride is a powerful hydride donor that reacts rapidly with nitriles to produce amines. 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. 1504 27 <<07b6cbcfb320354f8ff6148750fce7ec>]>> Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. 0000001890 00000 n 0000001748 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. This page looks at the reduction of nitriles to primary amines using either lithium tetrahydridoaluminate(III) (lithium aluminium hydride) or hydrogen and a metal catalyst. %PDF-1.4 %���� The reducing agent. nanoparticle catalyst 4 BH3-SMe2 is a more stable alternative. 0000005197 00000 n

0000003034 00000 n Ammonia borane as a reducing agent in organic synthesis. Despite its name, the structure of the reducing agent is very simple.

Please check your email for instructions on resetting your password. It also serves as an alternative way to navigate the website, and as a means of coming up with retrosynthetic ideas. Often NH3 (or NH4OH) is added to help minimize these by-pdts.[5]. The most commonly used approaches in nitriles hydrogenation are using strong hydride donors, such as lithium aluminum hydride, or catalytic hydrogenation.1However, these methods always lack chemoselectivity and

Once stabilized by a Lewis acid-base complexation the imine salt can accept a second hydride to form a dianion. 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. Any queries (other than missing content) should be directed to the corresponding author for the article. Activated samarium diiodide features excellent functional group tolerance and is therefore an attractive alternative to pyrophoric alkali metal hydrides. [1] 0000004060 00000 n 0000007531 00000 n O During this reaction the hydride nucleophile attacks the electrophilic carbon in the nitrile to form an imine anion. [1], Borane-tetrahydrofuran (BH3-THF) reduction of nitriles is typically performed in THF with heating. Number of times cited according to CrossRef: 3 d Transition Metal‐Catalyzed Hydrogenation of Nitriles and Alkynes. 0000011990 00000 n The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. Lithium Aluminum Hydride (LiAlH4) is a powerful hydride donor that reacts rapidly with nitriles to produce amines. 0000000016 00000 n

0000009359 00000 n As a service to our authors and readers, this journal provides supporting information supplied by the authors.

Activation of SmI 2 (Kagan’s reagent) with Lewis bases enables a mild general reduction of nitriles to primary amines under single electron transfer conditions. 0000002294 00000 n

The dianion can then be converted to an amine by addition of water.

and you may need to create a new Wiley Online Library account. The reaction map is intended to provide insight into possible reactions one step before and after the title reaction.

Click on the reaction arrow to visit the page. 0000014661 00000 n 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. Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user‐friendly cobalt complex, (Xantphos)CoCl2, is reported. Nitriles can be converted to 1° amines by reaction with LiAlH 4. 0000002455 00000 n

There are four hydrogens ("tetrahydido") around the aluminium in a negative ion (shown by the … 0000002266 00000 n 0000006649 00000 n The reduction of nitriles using LiAlH 4. 0000004301 00000 n One‐Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “on Water”.
Cooperative Molybdenum-Thiolate Reactivity for Transfer Hydrogenation of Nitriles, adsc201900586-sup-0001-misc_information.pdf. 0

3 Learn about our remote access options, Organometallic Synthesis and Catalysis Group, Chemical Engineering Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune, 411 008 India, Academy of Scientific and Innovative Research (AcSIR), CSIR-NCL, Pune, 411 008 India. 0000011214 00000 n 0000000854 00000 n %%EOF Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. 0000003775 00000 n Notably, an electron transfer from Sm(II) to bench stable nitrile precursors generates imidoyl-type … A Theoretical Investigation of Iron-Catalyzed Selective Hydrogenation of Nitriles to Secondary Imines.

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