Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

9.6K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
9.6K
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

691
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...
691
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.0K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

10.8K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
10.8K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

12.9K
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...
12.9K
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

5.0K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
5.0K

You might also read

Related Articles

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

Sort by
Same author

A General Approach to <i>geminal</i>-Dimethyl <i>trans</i>-Decalin Terpenoids.

Journal of the American Chemical Society·2026
Same author

A Unified Approach for the Synthesis of Conformationally Locked and sp<sup>2</sup>-sp<sup>3</sup> Fused Hybrids.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Driving Forces and Spin-Gated Reactivity of N5-Hydropyrimidopteridinetetraone Radicals in Photocatalysis.

The Journal of organic chemistry·2026
Same author

Stereodivergent Construction of <i>trans</i>-Decalin-Based Terpenoids.

Journal of the American Chemical Society·2026
Same author

FLP-type alkenylation of a phosphafluorene.

Dalton transactions (Cambridge, England : 2003)·2025
Same author

Enantioselective Total Syntheses of Sannamycins A and B.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Mar 11, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

8.4K

Arenophile-Mediated Dearomative Reduction.

Mikiko Okumura1, Stephanie M Nakamata Huynh1, Jola Pospech1

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Illinois, 61801, USA.

Angewandte Chemie (International Ed. in English)
|November 24, 2016
PubMed
Summary

This study introduces a novel visible-light method for arene dearomatization, creating unique cyclohexadiene and diaminocyclohexene compounds previously inaccessible through other dearomatization reactions.

Keywords:
arenesarenophilesdearomatizationfunctionalizationphotochemistry

More Related Videos

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
08:05

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Published on: October 7, 2020

6.7K
Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
13:59

Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins

Published on: December 12, 2013

6.7K

Related Experiment Videos

Last Updated: Mar 11, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

8.4K
Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O
08:05

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Published on: October 7, 2020

6.7K
Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
13:59

Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins

Published on: December 12, 2013

6.7K

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Dearomatization reactions are crucial for transforming aromatic compounds into valuable cyclic structures.
  • Existing dearomatization methods often lack efficiency or broad applicability.
  • Accessing functionalized cyclohexadienes and related structures remains a synthetic challenge.

Purpose of the Study:

  • To develop a new, efficient, and versatile dearomatization strategy for arenes.
  • To synthesize 1,3-cyclohexadienes and 1,4-diaminocyclohex-2-enes using a novel method.
  • To enable site-selective functionalization of complex aromatic systems.

Main Methods:

  • Visible-light-mediated cycloaddition of arenes with an N-N-arenophile.
  • In situ diimide reduction of the cycloadduct.
  • Subsequent cycloreversion or fragmentation to yield the desired products.

Main Results:

  • Successful dearomatization of simple arenes.
  • Synthesis of 1,3-cyclohexadienes and 1,4-diaminocyclohex-2-enes.
  • Demonstration of the method's applicability to polynuclear arenes.
  • Potential for further derivatization and site-selective functionalization.

Conclusions:

  • A novel visible-light-mediated dearomatization of arenes has been established.
  • The developed method provides access to previously inaccessible cyclohexadiene and diaminocyclohexene scaffolds.
  • This strategy offers significant potential for the synthesis of complex, functionalized aromatic derivatives.