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

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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...
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

You might also read

Related Articles

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

Sort by
Same author

Phase 2 Clinical Trial of MK-1942, a Negative Allosteric Modulator of Metabotropic Glutamate Receptor 2, for Treatment-Resistant Depression.

Journal of clinical psychopharmacology·2026
Same author

Adsorption of ultrashort-, short-, and long-chain per- and polyfluoroalkyl substances (PFAS): Impacts of adsorbent, PFAS type, and competitive ions.

Chemosphere·2026
Same author

Drug Development.

Alzheimer's & dementia : the journal of the Alzheimer's Association·2025
Same author

Biomarkers.

Alzheimer's & dementia : the journal of the Alzheimer's Association·2025
Same author

Benchmarking of Commercial Reverse Osmosis and Nanofiltration Membranes for Ultrashort-, Short-, and Long-Chain Perfluoroalkyl and Polyfluoroalkyl Substance Rejection.

Water environment research : a research publication of the Water Environment Federation·2025
Same author

Preclinical evaluation of MK-8189: A novel phosphodiesterase 10A inhibitor for the treatment of schizophrenia.

The Journal of pharmacology and experimental therapeutics·2025

Related Experiment Video

Updated: Jul 7, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Efficient amide-directed catalytic asymmetric hydroboration.

Sean M Smith1, Nathan C Thacker, James M Takacs

  • 1Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.

Journal of the American Chemical Society
|March 4, 2008
PubMed
Summary

This study demonstrates highly regioselective and enantioselective rhodium-catalyzed hydroboration of acyclic beta,gamma-unsaturated amides using chiral phosphite ligands and pinacolborane (PinBH). The method efficiently produces valuable beta-hydroxy amides with excellent enantiopurity.

More Related Videos

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Related Experiment Videos

Last Updated: Jul 7, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Acyclic beta,gamma-unsaturated amides are versatile synthetic intermediates.
  • Developing enantioselective methods for their functionalization is crucial for synthesizing chiral molecules.
  • Rhodium-catalyzed reactions offer powerful tools for selective transformations.

Purpose of the Study:

  • To develop a highly regioselective and enantioselective rhodium-catalyzed hydroboration of acyclic beta,gamma-unsaturated amides.
  • To identify efficient chiral ligands and reaction conditions for this transformation.
  • To demonstrate the synthesis of valuable beta-hydroxy amide products.

Main Methods:

  • Rhodium-catalyzed hydroboration using Rh(nbd)2BF4 and chiral monophosphite or phosphoramidite ligands.
  • Substrate scope exploration including disubstituted and trisubstituted alkenes.
  • Oxidation of intermediate boronate esters to beta-hydroxy amides.

Main Results:

  • Achieved high regioselectivity (>95%) and enantioselectivity (93-99% ee) in the hydroboration of various acyclic beta,gamma-unsaturated amides.
  • Identified BINOL-derived phosphoramidite 4 and TADDOL-derived phosphite 5c as highly effective ligands.
  • Demonstrated efficient synthesis of beta-hydroxy amides, exemplified by (S)-3-hydroxyhexanoic acid phenylamide in 80% yield and 99% ee.
  • Found N-phenyl amides and pinacolborane (PinBH) to be more efficient than their analogues and catecholborane, respectively.
  • Effective catalysis observed with moderate catalyst loading (0.5 mol %) and temperatures between 25-40 °C.

Conclusions:

  • A robust and efficient rhodium-catalyzed hydroboration protocol for acyclic beta,gamma-unsaturated amides has been established.
  • The developed method provides access to enantiomerically enriched beta-hydroxy amides with high regio- and stereocontrol.
  • The use of simple chiral phosphite ligands offers a practical approach for asymmetric synthesis.