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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Acid Halides to Ketones: Gilman Reagent

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the...

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...

Base-Promoted α-Halogenation of Aldehydes and Ketones

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base. The reaction begins with the abstraction of α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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Updated: Apr 21, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Ligand-controlled, tunable silver-catalyzed C-H amination.

Juliet M Alderson¹, Alicia M Phelps, Ryan J Scamp

¹Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society

|November 12, 2014

Summary

Researchers developed a new silver-catalyzed method for C-H amination. This approach allows for precise control over which C-H bonds react, offering a significant advancement in organic synthesis.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: June 20, 2014

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Catalyst-controlled C-H functionalization is crucial for efficient organic synthesis.
Achieving regioselectivity in C-H bond activation remains a significant challenge.

Purpose of the Study:

To develop a tunable and regioselective C-H functionalization reaction.
To demonstrate ligand control in silver-catalyzed nitrene transfer reactions.

Main Methods:

Utilized simple silver catalysts with common nitrogenated ligands.
Investigated nitrene transfer reactions targeting different C-H bonds.
Employed ligand tuning to control reaction selectivity.

Main Results:

Demonstrated successful ligand-controlled nitrene transfer.
Achieved site-selective C-H amination using silver catalysts.
Established the first example of ligand-controlled, site-selective silver-promoted C-H amination.

Conclusions:

Simple silver catalysts and nitrogenated ligands can effectively tune C-H functionalization.
This work provides a novel platform for regioselective C-H amination.
Advances the field of catalyst-controlled synthetic methodology.