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Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Reduction of Alkenes: Catalytic Hydrogenation

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...

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.

Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.

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Related Experiment Video

Updated: Mar 2, 2026

Determination of Glucan Chain Length Distribution of Glycogen Using the Fluorophore-Assisted Carbohydrate Electrophoresis FACE Method

Determination of Glucan Chain Length Distribution of Glycogen Using the Fluorophore-Assisted Carbohydrate Electrophoresis FACE Method

Published on: March 31, 2022

A novel carbohydrate labeling method utilizing transfer hydrogenation-mediated reductive amination.

Zsuzsanna Kovács¹, Gábor Papp², Henrietta Horváth³

¹Horváth Csaba Laboratory of Bioseparation Sciences, University of Debrecen, Hungary.

Journal of Pharmaceutical and Biomedical Analysis

|May 24, 2017

Summary

A novel catalytic method using iridium and ruthenium complexes offers a safer, greener alternative for labeling glycans in biopharmaceutical analysis. This approach avoids hazardous byproducts, improving safety and efficiency in glycan analysis.

Keywords:

Biopharmaceuticals Fluorophore labeling N-glycans Transfer hydrogenation

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Determination of Glucan Chain Length Distribution of Glycogen Using the Fluorophore-Assisted Carbohydrate Electrophoresis FACE Method

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Published on: March 31, 2022

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Activation and Conjugation of Soluble Polysaccharides using 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate CDAP

Activation and Conjugation of Soluble Polysaccharides using 1-Cyano-4-Dimethylaminopyridine Tetrafluoroborate CDAP

Published on: June 14, 2021

Area of Science:

Biochemistry and Analytical Chemistry
Biotechnology and Biopharmaceutical Analysis

Background:

Capillary electrophoresis with laser-induced fluorescence (CE-LIF) is a key technique for high-resolution glycan analysis.
Traditional glycan labeling involves reductive amination with sodium cyanoborohydride, which generates hazardous hydrogen cyanide (HCN) in large-scale biopharmaceutical applications.

Purpose of the Study:

To develop a safer and environmentally friendly alternative to sodium cyanoborohydride for glycan labeling in CE-LIF.
To evaluate the efficacy of catalytic hydrogen transfer using water-soluble iridium(III) and ruthenium(II)-phosphine complexes for carbohydrate labeling.

Main Methods:

Investigated catalytic hydrogen transfer from formic acid using novel water-soluble iridium(III) and ruthenium(II)-phosphine complexes.
Assessed catalytic activity and efficiency in labeling various standard carbohydrate and N-glycan structures (fetuin, ribonuclease B, human plasma).

Main Results:

Iridium(III) and ruthenium(II) complexes demonstrated high catalytic activity for carbohydrate labeling.
The catalytic method achieved labeling efficiencies comparable to sodium cyanoborohydride.
Derivatization reaction times were rapid (<20 min) with no observed bias for different glycan structures.

Conclusions:

Catalytic hydrogen transfer offers a safe, efficient, and environmentally friendly alternative for glycan labeling in biopharmaceutical analysis.
This method reduces health risks associated with traditional reagents like sodium cyanoborohydride, particularly in large-scale applications.