Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...

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...

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...

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...

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Loss of Carboxy Group as CO₂: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Synthesis of 9-(Piperidin-3-yl)purine Derivatives <i>via</i> [4 + 2] Cycloaddition of Aza-π-allylpalladium 1,4-Dipole.

Organic letters·2026

Same author

Catalytic Asymmetric Nucleophilic Amination and Kinetic Resolution of α-Bromo-acylpyrazoles.

Organic letters·2026

Same author

Engineering Enantiocomplementary Protoglobins for Stereoconvergent Construction of <i>N</i>-Alkylated α-Aminoketones.

Journal of the American Chemical Society·2026

Same author

Integrating DFT and Machine Learning for Mechanistic Elucidation and Catalyst Optimization in DAP-Catalyzed Asymmetric Aza-Mislow-Evans Reactions.

The journal of physical chemistry letters·2026

Same author

Imidazolidine-Pyrroloimidazolone Pyridine-Cu(OTf)<sub>2</sub> Complex Catalyzed Asymmetric Radical Carbo-Esterification.

Organic letters·2026

Same author

Catalytic asymmetric sulfonimidoyl transfer to access chiral sulfonimidoyl fluorides and related derivatives.

Nature chemistry·2026

Search research articles

Related Experiment Video

Updated: Jun 6, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

NADH Analogues Enable Metal- and Light-Free Decarboxylative Functionalization.

Lei Liang^1,2, Yue-Hui Wang¹, Cheng-Xing Cui¹

¹School of Chemistry and Chemical Engineering, Henan Institute of Science and Technology Hualan Avenue East Section, Xinxiang, Henan Province, 453007, China E-mails.

Angewandte Chemie (International Ed. in English)

|November 25, 2024

Summary

This study introduces a rapid, metal- and light-free method for decarboxylative functionalization using reduced nicotinamide adenine dinucleotide (NADH) analogues. The approach enables diverse bond formation and streamlines the synthesis of valuable sp3 carbon-enriched compounds.

Keywords:

NADH analogues biomimetic transformation decarboxylative functionalization metal- and light-free

More Related Videos

Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

Related Experiment Videos

Last Updated: Jun 6, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Decarboxylative reactions are crucial in organic synthesis.
Metal- and light-mediated methods often present limitations.
Developing efficient, metal-free alternatives is highly desirable.

Purpose of the Study:

To develop a novel metal- and light-free decarboxylative functionalization strategy.
To enable efficient bond formation using reduced nicotinamide adenine dinucleotide (NADH) analogues.
To streamline the synthesis of sp3 carbon-enriched compounds.

Main Methods:

Utilized reduced nicotinamide adenine dinucleotide (NADH) analogues.
Employed in situ preparation of aryliodine(III) dicarboxylates.
Conducted reactions under open-air and ambient conditions within 5 minutes.

Main Results:

Achieved efficient and operationally simple decarboxylative functionalization.
Demonstrated a broad substrate scope with over 70 examples.
Successfully applied the method for late-stage functionalization of drug molecules and natural products.
Elucidated the mechanistic pathway through experimental and computational studies.

Conclusions:

The developed method offers a new dimension to classical decarboxylative reactions.
Provides a streamlined synthesis for sp3 carbon-enriched compounds.
Highlights the synthetic utility and broad applicability of the novel approach.