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

Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.5K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
4.5K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

3.3K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
3.3K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.0K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.2K
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

23.9K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
23.9K
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

17.2K
Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
17.2K

You might also read

Related Articles

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

Sort by
Same author

Prolyl 4-Hydroxylase: Substrate Isosteres in Which an (E)- or (Z)-Alkene Replaces the Prolyl Peptide Bond.

Biochemistry·2016
Same author

Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst.

Organic & biomolecular chemistry·2016
Same author

Diazo groups endure metabolism and enable chemoselectivity in cellulo.

Journal of the American Chemical Society·2015
Same author

Diazo compounds for the bioreversible esterification of proteins.

Chemical science·2014
Same author

Facile chemical functionalization of proteins through intein-linked yeast display.

Bioconjugate chemistry·2013
Same author

Diazo Compounds as Highly Tunable Reactants in 1,3-Dipolar Cycloaddition Reactions with Cycloalkynes().

Chemical science·2012

Related Experiment Video

Updated: Jan 30, 2026

An In Vitro Enzymatic Assay to Measure Transcription Inhibition by GalliumIII and H3 5,10,15-trispentafluorophenylcorroles
09:00

An In Vitro Enzymatic Assay to Measure Transcription Inhibition by GalliumIII and H3 5,10,15-trispentafluorophenylcorroles

Published on: March 18, 2015

12.1K

Tris(pentafluorophenyl)borane-Catalyzed Reactions Using Silanes.

Taylor Hackel1, Nicholas A McGrath2

  • 1Department of Chemistry and Biochemistry, University of Wisconsin⁻La Crosse, La Crosse, WI 54601, USA. hackel.taylor@uwlax.edu.

Molecules (Basel, Switzerland)
|January 30, 2019
PubMed
Summary

Tris(pentafluorophenyl)borane, a stable Lewis acid, efficiently catalyzes reductions of alcohols and carbonyls using silanes. This review highlights its utility in various powerful chemical transformations, even with water present.

Keywords:
Lewis acidSi-H activationcarbonyl reductionmechanismsilanestereoselectivetris(pentafluorophenyl)borane

More Related Videos

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K
Protease- and Acid-catalyzed Labeling Workflows Employing 18O-enriched Water
09:43

Protease- and Acid-catalyzed Labeling Workflows Employing 18O-enriched Water

Published on: February 20, 2013

12.3K

Related Experiment Videos

Last Updated: Jan 30, 2026

An In Vitro Enzymatic Assay to Measure Transcription Inhibition by GalliumIII and H3 5,10,15-trispentafluorophenylcorroles
09:00

An In Vitro Enzymatic Assay to Measure Transcription Inhibition by GalliumIII and H3 5,10,15-trispentafluorophenylcorroles

Published on: March 18, 2015

12.1K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K
Protease- and Acid-catalyzed Labeling Workflows Employing 18O-enriched Water
09:43

Protease- and Acid-catalyzed Labeling Workflows Employing 18O-enriched Water

Published on: February 20, 2013

12.3K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Lewis acids are crucial catalysts in organic synthesis.
  • Tris(pentafluorophenyl)borane is a highly reactive yet air-stable Lewis acid.
  • Its stability and reactivity profile offer advantages over traditional Lewis acids like boron trichloride.

Purpose of the Study:

  • To review the catalytic applications of tris(pentafluorophenyl)borane.
  • To focus on reactions employing silanes as stoichiometric reductants.
  • To highlight the reduction of alcohols, carbonyls, and carbonyl-like derivatives.

Main Methods:

  • Utilizing tris(pentafluorophenyl)borane as a Lewis acid catalyst.
  • Employing silanes as stoichiometric reductants.
  • Investigating catalytic reductions of various functional groups.

Main Results:

  • Demonstrated high reactivity comparable to boron trichloride.
  • Showcased exceptional stability, including tolerance to water.
  • Facilitated powerful catalytic transformations in organic synthesis.

Conclusions:

  • Tris(pentafluorophenyl)borane is a versatile and robust Lewis acid catalyst.
  • Its combination with silanes enables efficient reductions.
  • Offers a practical alternative for various synthetic procedures.