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Related Concept Videos

Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.2K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.2K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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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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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.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
2.9K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.2K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Reframing primary alkyl amines as aliphatic building blocks.

Kathleen J Berger1, Mark D Levin

  • 1Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, USA. marklevin@uchicago.edu.

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|October 20, 2020
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Primary aliphatic amines, traditionally inert, are now valuable C(sp3) synthons. This review covers advances in aliphatic deamination chemistry, including cross-coupling and photocatalyzed reactions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Primary aliphatic amines are common in natural products but difficult to functionalize.
  • Traditional substitution chemistry considers these amines unreactive.

Purpose of the Study:

  • To review recent advances in aliphatic deamination chemistry.
  • To highlight the utility of amines as C(sp3) synthons.
  • To compare various synthetic methodologies.

Main Methods:

  • Review of cross-coupling reactions.
  • Analysis of photocatalyzed transformations.
  • Comparison of oxidative deamination and transition metal-catalyzed reactions.

Main Results:

  • Aliphatic amines can be effectively transformed using deamination reactions.
  • Diverse synthetic strategies enable the use of amines as versatile building blocks.
  • Polar and radical mechanisms are key to these transformations.

Conclusions:

  • Aliphatic deamination chemistry offers powerful new synthetic routes.
  • Amines are valuable and versatile C(sp3) synthons.
  • Recent advances expand the synthetic chemist's toolkit.