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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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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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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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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 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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Structure of Amines01:19

Structure of Amines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
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Amines: Introduction01:07

Amines: Introduction

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

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Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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Robust Buchwald-Hartwig amination enabled by ball-milling.

Qun Cao1, William I Nicholson, Andrew C Jones

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|September 19, 2018
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Summary

A new mechanochemical approach simplifies palladium-catalyzed Buchwald-Hartwig amination using a Pd PEPPSI catalyst. This method efficiently couples aryl halides with secondary amines, showing broad substrate scope and potential for aerobic conditions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Buchwald-Hartwig amination is a crucial C-N bond-forming reaction.
  • Traditional methods often require harsh conditions or specific solvents.
  • Mechanochemistry offers a solvent-free alternative for organic synthesis.

Purpose of the Study:

  • To develop a simple and efficient mechanochemical method for Buchwald-Hartwig amination.
  • To utilize a palladium PEPPSI catalyst system for this transformation.
  • To investigate the reaction's performance under aerobic conditions.

Main Methods:

  • Mechanochemical synthesis using ball milling.
  • Palladium-catalyzed Buchwald-Hartwig amination of aryl halides with secondary amines.
  • Use of a specific palladium PEPPSI catalyst system.
  • Testing on a diverse range of 30 substrates.
  • Comparison of aerobic conditions in solution versus mechanochemical settings.

Main Results:

  • Successful development of an operationally simple mechanochemical Buchwald-Hartwig amination.
  • Demonstration of broad substrate scope across 30 different aryl halide and secondary amine combinations.
  • Application of the method in a relevant target synthesis.
  • Insights into the reaction's behavior under aerobic conditions in both solution and mechanochemical formats.

Conclusions:

  • Mechanochemistry provides a viable and efficient alternative for palladium-catalyzed Buchwald-Hartwig amination.
  • The Pd PEPPSI catalyst system is effective under mechanochemical conditions.
  • The developed method offers advantages in terms of operational simplicity and potential for greener synthesis.