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

Oxidation-Reduction Reactions

Oxidation-Reduction Reactions

Oxidation–Reduction Reactions

Phase I Reactions: Reductive Reactions

Phase I Reactions: Reductive Reactions

Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

Redox Reactions

Redox Reactions

Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...

Synthesis and Decomposition Reactions

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.

You might also read

Related Articles

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

Sort by

Same author

Unified Synthesis of Unconventional α-Polyhalogenated Amines Through Hydroaminoalkylation.

Angewandte Chemie (International ed. in English)·2026

Same author

An alkyl-swap platform for late-stage modification of secondary N-methylamines.

Nature chemistry·2026

Same author

Cation Sampling Enables Regiodivergent Distal Functionalization of Ketones.

Journal of the American Chemical Society·2026

Same author

Target-agnostic SAR mapping and immunological evaluation of (-)-FR252921 and analogs against primary human immune cells.

Chemical science·2026

Same author

Intrinsic N-Terminal Reactivity and Improved Analysis of DSSO-Carbamate and Carbamate-Based Cross-Linkers.

Analytical chemistry·2026

Same author

Deprotective Functionalization: An Emerging Concept for Amine Reactivity.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025

Search research articles

Related Experiment Video

Updated: Feb 14, 2026

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Published on: March 18, 2012

A Stereoselective Reductive Hosomi-Sakurai Reaction.

Adriano Bauer¹, Nuno Maulide¹

¹Institute of Organic Chemistry, University of Vienna , Währinger Straße 38, 1090 Vienna, Austria.

Organic Letters

|February 23, 2018

Summary

A new reductive Hosomi-Sakurai reaction offers a mild, stereoselective method for synthesizing valuable products. This efficient transformation simplifies complex syntheses, including a key step towards an acetylcholinesterase (AChE) inhibitor.

More Related Videos

Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions

Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions

Published on: July 3, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Related Experiment Videos

Last Updated: Feb 14, 2026

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Published on: March 18, 2012

Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions

Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions

Published on: July 3, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

Organic Chemistry
Synthetic Methodology
Redox Reactions

Background:

The Hosomi-Sakurai reaction is a cornerstone of allylation chemistry.
Developing novel variants expands synthetic capabilities.
Redox-neutral transformations are desirable for efficiency and sustainability.

Purpose of the Study:

To report a novel reductive variant of the Hosomi-Sakurai reaction.
To establish a mild, stereoselective method for internal reduction.
To demonstrate the synthetic utility of this new transformation.

Main Methods:

Utilizing readily available starting materials.
Employing a redox-neutral, stereoselective internal reduction.
Performing the reaction under mild conditions.

Main Results:

Achieved a novel reductive Hosomi-Sakurai reaction.
Obtained useful products with high diastereoselectivities (up to 7:1).
Demonstrated operational simplicity and mild reaction conditions.

Conclusions:

The developed method provides a versatile and efficient route to complex molecules.
This reductive variant expands the scope of Hosomi-Sakurai reactions.
The method is applicable to the stereoselective synthesis of biologically relevant compounds, such as acetylcholinesterase inhibitors.