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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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A dual site catalyst for mild, selective nitrile reduction.

Zhiyao Lu1, Travis J Williams

  • 1Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. travisw@usc.edu.

Chemical Communications (Cambridge, England)
|January 11, 2014
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Summary

Researchers developed a new ruthenium catalyst using a bis(pyrazolyl)borate scaffold. This catalyst enables cooperative reduction, with boron and ruthenium centers working together for selective nitrile reduction.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis Science

Background:

  • Ruthenium complexes are widely studied for catalytic applications.
  • Nitrile reduction is a key transformation in organic synthesis.
  • Developing catalysts with novel reactivity and selectivity is an ongoing challenge.

Purpose of the Study:

  • To report a novel ruthenium bis(pyrazolyl)borate scaffold.
  • To demonstrate its cooperative reduction reactivity for selective nitrile reduction.
  • To synthesize and characterize the pre-catalyst compound.

Main Methods:

  • Synthesis of the pre-catalyst compound [κ(3)-(1-pz)2HB(N = CHCH3)]Ru(cymene)(+) TfO(-).
  • Utilizing readily-available starting materials.
  • Employing a straightforward synthetic route.

Main Results:

  • A novel ruthenium bis(pyrazolyl)borate scaffold was successfully synthesized.
  • The scaffold enables cooperative reduction reactivity.
  • Boron and ruthenium centers work in concert for selective nitrile reduction.

Conclusions:

  • The synthesized pre-catalyst is an appealing option for various catalytic reactions.
  • This novel scaffold offers a new platform for designing cooperative catalysts.
  • The cooperative action of boron and ruthenium centers provides enhanced reactivity and selectivity.