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

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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...
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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

Preparation of Amines: Reduction of Amides and Nitriles

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,...

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Published on: February 16, 2020

Fast reductive amination by transfer hydrogenation "on water".

Qian Lei1, Yawen Wei, Dinesh Talwar

  • 1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, PR China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 13, 2013
PubMed
Summary

This study introduces a new method for reductive amination that uses water as a solvent instead of traditional organic solvents. The method uses a cyclometallated iridium catalyst and formate as a hydrogen source. The researchers found that a pH of 4.8 is optimal for high catalytic activity and chemoselectivity. The reaction is faster in water than in organic solvents and allows for a higher substrate-to-catalyst ratio than previously reported. The method is practical and environmentally friendly, enabling the synthesis of a wide range of amine compounds in high yields.

Keywords:
Reductive aminationTransfer hydrogenationAqueous catalysisIridium catalysts

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Area of Science:

  • Organic chemistry synthesis methods
  • Catalytic transfer hydrogenation in aqueous media
  • Green chemistry and sustainable synthesis

Background:

Many chemical syntheses rely on organic solvents, which can be costly and environmentally harmful. Prior research has shown that transfer hydrogenation is an effective method for reductive amination, but most studies use non-aqueous systems. No prior work had resolved the optimal pH for high chemoselectivity and activity in aqueous reductive amination. This gap motivated the search for a more efficient and environmentally friendly approach. The researchers propose that using water as a solvent could reduce costs and environmental impact. However, the effectiveness of aqueous transfer hydrogenation for reductive amination remained unclear. The need for a catalyst that functions well in water was also unmet. This study addresses these uncertainties by exploring a new protocol.

Purpose Of The Study:

The aim of this study is to develop a reductive amination method that operates efficiently in water. The specific problem is the inefficiency and environmental drawbacks of traditional organic solvent-based reductive amination. The motivation is to create a more sustainable and practical synthesis route. The researchers propose that using a cyclometallated iridium catalyst and formate as a hydrogen source could achieve this goal. The study seeks to determine the optimal pH for high catalytic activity and chemoselectivity. It also aims to test the scalability of the reaction by increasing the substrate-to-catalyst ratio. The researchers propose that an aqueous system could offer faster reaction rates and higher yields. This approach could provide a practical alternative to current methods.

Main Methods:

The study uses cyclometallated iridium complexes as catalysts and formate as the hydrogen source. The reactions are carried out in an aqueous solution. The pH of the solution is systematically varied to determine its effect on catalytic activity and chemoselectivity. The best pH value is identified as 4.8. The researchers compare the reaction rates in aqueous and organic solvent systems. The substrate-to-catalyst ratio is tested up to 1×10⁵, which is the highest reported in reductive amination. A wide range of ketones and aldehydes are tested for compatibility with various amines. The yields of the resulting amine compounds are measured to assess the effectiveness of the method.

Main Results:

The highest catalytic activity and chemoselectivity are observed at pH 4.8. The reaction rate in aqueous solution is faster than in organic solvents. The substrate-to-catalyst ratio reaches 1×10⁵, which is the highest ever reported for reductive amination. The catalyst is accessible and the reaction is operationally simple. A wide range of ketones and aldehydes react successfully with various amines. The yields of the resulting amine compounds are high. The method is practical and environmentally friendly. These findings suggest that aqueous transfer hydrogenation is a viable alternative to traditional methods.

Conclusions:

The authors propose that the optimal pH for high catalytic activity and chemoselectivity is 4.8. The aqueous system allows for a higher substrate-to-catalyst ratio than previously reported. The reaction is faster in water than in organic solvents. The method is practical and environmentally friendly. The catalyst is easy to access and the reaction is operationally simple. A wide range of ketones and aldehydes can react with various amines in high yields. The protocol provides a new method for the synthesis of amine compounds. The authors suggest that this approach could be useful in industrial and academic settings.

The method achieves high yields of amine compounds using an aqueous system with a substrate-to-catalyst ratio of 1×10⁵.

Formate is used because it is a safe and environmentally friendly alternative to traditional hydrogen sources.

The authors propose that pH 4.8 is optimal for high catalytic activity and chemoselectivity in the aqueous system.

The aqueous system is faster and allows for a higher substrate-to-catalyst ratio than organic solvent methods.

A wide range of ketones and aldehydes can react with various amines to form amine compounds.

The authors propose that the method is environmentally friendly and practical for industrial use.