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Related Concept Videos

Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.3K
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.
6.3K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.0K
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,...
3.0K
Preparation of Amides01:29

Preparation of Amides

4.0K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.0K
Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

75.3K
Oxidation–Reduction Reactions
75.3K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.4K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.4K
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...
3.4K

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Predicting Catalyst Extrudate Breakage Based on the Modulus of Rupture
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A BEt3-Base Catalyst for Amide Reduction with Silane.

Wubing Yao1, Huaquan Fang1, Qiaoxing He1,2

  • 1State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

The Journal of Organic Chemistry
|April 24, 2019
PubMed
Summary

A new catalytic system using triethylborane (BEt3) and a base efficiently reduces amides to amines under mild conditions. This method also allows selective conversion of amides to imines or nitriles.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Amide reduction is a fundamental transformation in organic synthesis.
  • Existing methods often require harsh conditions or expensive reagents.
  • Development of efficient and selective catalytic systems is highly desirable.

Purpose of the Study:

  • To develop a simple and practical catalytic system for selective amide reduction.
  • To explore the scope and limitations of the developed catalytic system.
  • To investigate the mechanism of the catalytic amide hydrosilylation.

Main Methods:

  • Catalytic reduction of amides using hydrosilane or hydrosiloxane.
  • Employing triethylborane (BEt3) as a catalyst with an alkali metal base.
  • Exploring selective transformations of primary and secondary amides.

Main Results:

  • Successful reduction of tertiary, secondary, and primary amides to amines under mild conditions.
  • Selective synthesis of aldimines from secondary amides and nitriles from primary amides.
  • Demonstrated broad scope of the BEt3-base-catalyzed amide hydrosilylation reactions.

Conclusions:

  • A cost-effective and versatile catalytic system for amide transformations has been developed.
  • The catalytic system offers mild reaction conditions and high selectivity.
  • Mechanistic studies suggest a novel Si-H···B activation pathway involving hydride abstraction.