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

Hydroboration-Oxidation of Alkenes

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.

Regioselectivity and Stereochemistry of Hydroboration

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.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

IR Frequency Region: Alkyne and Nitrile Stretching

IR Frequency Region: Alkyne and Nitrile Stretching

Both alkyne (C≡C) and nitrile (C≡N) functional groups contain triple bonds and show stretching absorptions around the wavenumber range of 2100 to 2300 cm−1 in the diagnostic region of the IR spectra.
Comparing the stretching vibrational frequency of C≡C triple bonds with that of double and single bonds, it is evident that C≡C triple bonds exhibit a higher stretching frequency than C=C double and C–C single bonds. Similarly, the C≡N triple bond...

You might also read

Related Articles

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

Sort by

Same author

Untapped catalytic ability of aluminium has been unlocked.

Nature·2026

Same author

Cationic and Neutral Heterometallic Ir-Group 12 Element Polyhydride Compounds: Synthesis, Structure and Reactivity.

Inorganic chemistry·2026

Same author

A direct comparison of lithium tetra(<i>n</i>-butyl) manganate(II) and magnesiate: structural insights and catalytic hydroamination of styrenes.

Chemical communications (Cambridge, England)·2025

Same author

Reactivity of Cyclopropenylaluminates.

Organometallics·2025

Same author

Synthesis and characterization of Sn(II) complexes supported by amino bis-phenoxide ligands.

Dalton transactions (Cambridge, England : 2003)·2025

Same author

Structural and Gas Uptake Studies on Iron(II) β‑Diketiminate Metallomacrocycles.

Organometallics·2025

Same journal

Enhanced and selective oxygen reduction by iron porphyrin with a biguanide residue in the second coordination sphere.

Chemical science·2026

Same journal

Excited-state orbital angular momentum enables all-optical molecular spin coherence.

Chemical science·2026

Same journal

Polyvinyl-based hole-transporting materials processed with non-destructive and green solvents for tin-lead perovskite solar cells and all-perovskite tandems.

Chemical science·2026

Same journal

Pd-catalyzed regio- and enantioselective allylation of cyclic allylboronates.

Chemical science·2026

Same journal

Covalent polyoxometalate-polyimide hybridization: multi-scale molecular engineering toward high-performance sodium-ion battery anodes.

Chemical science·2026

Same journal

Catalytic visible light-driven alkane dehydrogenation by a di-uranyl germanotungstate.

Chemical science·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Feb 9, 2026

Biodegradable Magnesium Stent Treatment of Saccular Aneurysms in a Rat Model - Introduction of the Surgical Technique

Biodegradable Magnesium Stent Treatment of Saccular Aneurysms in a Rat Model - Introduction of the Surgical Technique

Published on: October 1, 2017

Magnesium-catalysed nitrile hydroboration.

Catherine Weetman¹, Mathew D Anker¹, Merle Arrowsmith¹

¹Department of Chemistry , University of Bath , Claverton Down , Bath , BA2 7AY , UK .

Chemical Science

|June 14, 2018

Summary

This summary is machine-generated.

A novel magnesium complex selectively catalyzes the reductive hydroboration of nitriles using pinacolborane (HBpin). Mechanistic studies reveal distinct pathways for different nitrile types, highlighting the versatility of heavier alkaline earth catalysis.

More Related Videos

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

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

Published on: February 20, 2013

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Related Experiment Videos

Last Updated: Feb 9, 2026

Biodegradable Magnesium Stent Treatment of Saccular Aneurysms in a Rat Model - Introduction of the Surgical Technique

Biodegradable Magnesium Stent Treatment of Saccular Aneurysms in a Rat Model - Introduction of the Surgical Technique

Published on: October 1, 2017

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

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

Published on: February 20, 2013

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Area of Science:

Organometallic Chemistry
Catalysis
Boron Chemistry

Background:

Reductive hydroboration of nitriles is a key transformation in organic synthesis.
Developing selective and efficient precatalysts is crucial for advancing catalytic methods.
Magnesium complexes offer a promising avenue for earth-abundant metal catalysis.

Purpose of the Study:

To present a β-diketiminato n-butylmagnesium complex as a selective precatalyst for nitrile hydroboration.
To elucidate the catalytic mechanism and identify key intermediates.
To investigate the influence of substrate electronic properties on the reaction pathway.

Main Methods:

Stoichiometric reactivity studies to identify intermediates.
Kinetic studies to determine reaction orders and rate dependencies.
Kinetic isotope effect (KIE) measurements using deuterium-labeled pinacolborane (DBpin).

Main Results:

The precatalyst selectively mediates the reductive hydroboration of organic nitriles with pinacolborane (HBpin).
Catalytic turnover involves magnesium aldimido, aldimidoborate, and borylamido intermediates.
Mechanisms vary based on nitrile substitution, with distinct rate-determining steps and HBpin involvement observed for alkyl, electron-donating aryl, and electron-withdrawing aryl nitriles.
Kinetic isotope effects indicate B-H bond breaking and C-H bond formation in rate-determining steps for alkyl and electron-donating aryl nitriles.

Conclusions:

A common mechanistic framework is proposed, with rate-determining steps influenced by pre-equilibria and substrate basicity.
The study reveals significant mechanistic diversity in homogeneous heavier alkaline earth catalysis.
This work expands the scope of magnesium-catalyzed transformations and provides insights into catalytic cycles involving nitrile substrates.