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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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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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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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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.4K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.4K
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...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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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.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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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.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent.

Oleg I Afanasyev1, Dmitry L Usanov, Denis Chusov

  • 1A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 119991, Vavilova St 28, Moscow, Russian Federation. chusov@ineos.ac.ru denis.chusov@gmail.com.

Organic & Biomolecular Chemistry
|November 30, 2017
PubMed
Summary

A new solvent-free reductive amination method uses iron pentacarbonyl as a reducing agent, eliminating the need for external hydrogen sources or catalysts. This efficient process works with various substrates, including less reactive ones like benzophenone.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Reductive amination is a key transformation in organic synthesis.
  • Traditional methods often require external hydrogen sources or specific catalysts, limiting their applicability and sustainability.

Purpose of the Study:

  • To develop a novel, efficient, and sustainable reductive amination protocol.
  • To eliminate the need for external hydrogen sources and catalysts in reductive amination.

Main Methods:

  • Utilized iron pentacarbonyl as a sole reducing agent.
  • Conducted the reaction under solvent-free conditions.
  • Employed a range of carbonyl compounds and amines as substrates.

Main Results:

  • Successfully achieved solvent-free reductive amination without external hydrogen or catalysts.
  • Demonstrated broad substrate scope, including challenging substrates like benzophenone.
  • Showcased tolerance to various functional groups, including bromo-, cyano-, benzyloxy-, pyrimidyl, and styryl moieties.

Conclusions:

  • Iron pentacarbonyl is an effective and versatile reducing agent for reductive amination.
  • The developed method offers a greener and more practical alternative to existing protocols.
  • This approach expands the synthetic utility of reductive amination for complex molecule synthesis.