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Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.

Preparation of Amines: Reduction of Amides and Nitriles

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,...

Nitriles to Amines: LiAlH4 Reduction

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...

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

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Electrochemically Enabled, Nickel-Catalyzed Amination.

Chao Li¹, Yu Kawamata¹, Hugh Nakamura¹

¹The Scripps Research Institute (TSRI), North Torrey Pines Road, La Jolla, CA, 92037, USA.

Angewandte Chemie (International Ed. in English)

|August 24, 2017

Summary

This summary is machine-generated.

Electrochemistry offers a new way to create essential chemical bonds using nickel catalysts. This method is scalable, fast, and works with various starting materials, providing a valuable alternative for medicinal chemistry.

Keywords:

amination arylation cross-coupling electrochemistry nickel

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Electrochemistry

Background:

Buchwald-Hartwig-Ullmann-type amination is crucial in medicinal chemistry for forming aryl-amine bonds.
Traditional methods often require specific conditions or expensive catalysts.

Purpose of the Study:

To explore electrochemistry as a complementary method for Buchwald-Hartwig-Ullmann-type amination.
To develop a cost-effective and mild catalytic system for C-N bond formation.

Main Methods:

Utilizing electrochemistry with an inexpensive nickel catalyst.
Employing various aryl halides (Ar-Cl, Ar-Br, Ar-I, Ar-OTf) and amine types (primary and secondary).
Investigating alternative X-H donors like alcohols and amides.

Main Results:

Demonstrated the potential of electrochemistry for aryl halide amination.
Achieved mild reaction conditions, high scalability, and broad functional-group tolerance.
Showcased the reaction's rapid rate and versatility with diverse substrates.

Conclusions:

Electrochemical Buchwald-Hartwig-Ullmann-type amination provides a sustainable and efficient alternative.
This method expands the synthetic toolbox for medicinal chemists.
The nickel-catalyzed electrochemical approach offers a mild, scalable, and versatile route to C-N bond formation.