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Related Concept Videos

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
4.1K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

5.2K
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...
5.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.7K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
9.7K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.3K
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.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.3K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

15.3K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Ruthenium-catalyzed reductive amination without an external hydrogen source.

Pavel N Kolesnikov1, Niyaz Z Yagafarov, Dmitry L Usanov

  • 1A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 119991, Vavilova St. 28, Moscow, Russian Federation.

Organic Letters
|January 1, 2015
PubMed
Summary
This summary is machine-generated.

Ruthenium catalysts enable reductive amination using carbon monoxide as a hydrogen-free reductant. This novel method efficiently synthesizes the antianxiety drug ladasten.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Reductive amination is a key transformation in organic synthesis.
  • Traditional methods often require external hydrogen sources, posing safety and handling challenges.
  • Developing sustainable and efficient synthetic routes is crucial for pharmaceutical development.

Purpose of the Study:

  • To develop a novel ruthenium-catalyzed reductive amination protocol.
  • To utilize carbon monoxide as a reductant, eliminating the need for external hydrogen.
  • To demonstrate the application of this method in the synthesis of a pharmaceutical compound.

Main Methods:

  • Employing ruthenium(III) chloride as a catalyst (0.008-2 mol %).
  • Utilizing carbon monoxide (CO) as the sole reductant.
  • Applying the developed method to the synthesis of the antianxiety agent ladasten.

Main Results:

  • Successfully achieved ruthenium-catalyzed reductive amination without an external hydrogen source.
  • Demonstrated the efficacy of carbon monoxide as a viable reductant in this transformation.
  • Synthesized the target antianxiety agent ladasten using the developed protocol.

Conclusions:

  • A new, hydrogen-free reductive amination method has been established using ruthenium catalysis and carbon monoxide.
  • This approach offers a more sustainable and potentially safer alternative to conventional methods.
  • The protocol is effective for the synthesis of valuable pharmaceutical compounds like ladasten.