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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene 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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

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Updated: Jul 13, 2025

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

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Published on: June 21, 2017

Catalytic Alkyne Allylboration: A Quest for Selectivity.

Andrea Chaves-Pouso¹, Eva Rivera-Chao¹, Martín Fañanás-Mastral¹

¹Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.

ACS Catalysis

|October 12, 2023

Summary

This perspective details catalytic allylboration of alkynes, a key method for creating complex organic molecules. These reactions offer stereoselective synthesis of diverse, functionalized building blocks for advanced chemistry.

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

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

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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

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

Published on: February 16, 2020

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Catalytic methodologies are crucial for synthesizing complex organic molecules from simple precursors.
Multicomponent carboboration reactions are valuable for generating molecular diversity through stereoselective synthesis of functionalized building blocks.

Purpose of the Study:

To review developments in catalytic allylboration of alkynes.
To highlight strategies for controlling selectivity in these transformations.

Main Methods:

Focuses on catalytic allylboration reactions involving alkynes.
Discusses methods for achieving regio-, diastereoselecto-, and enantioselectivity.

Main Results:

Catalytic allylboration of alkynes provides stereoselective access to functionalized building blocks.
Key features enabling control over selectivity in these reactions are identified.

Conclusions:

Catalytic allylboration of alkynes is a powerful strategy for molecular synthesis.
This method significantly contributes to achieving molecular diversity with high selectivity.