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Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

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...

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.

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.

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.

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.

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Updated: Nov 4, 2025

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

Borrowing Hydrogen for Organic Synthesis.

Benjamin G Reed-Berendt¹, Daniel E Latham¹, Mubarak B Dambatta¹

¹Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, U.K.

ACS Central Science

|May 31, 2021

Summary

This summary is machine-generated.

Borrowing hydrogen chemistry utilizes catalysts to transform alcohols into valuable products, with water as the only byproduct. This versatile one-pot method offers diverse synthetic applications and is advancing rapidly.

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Hydrogen Production and Utilization in a Membrane Reactor

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

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Hydrogen Production and Utilization in a Membrane Reactor

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Borrowing hydrogen chemistry enables the synthetic diversification of commodity alcohols.
This process involves catalyst-mediated oxidation of alcohols to carbonyl intermediates, followed by further transformations and hydrogen transfer.

Purpose of the Study:

To highlight the diversity of catalysts and transformations in borrowing hydrogen chemistry.
To showcase recent significant advances and the versatility of this synthetic approach.

Main Methods:

Review and synthesis of recent literature on borrowing hydrogen reactions.
Focus on metal and biocatalysts for alcohol functionalization.
Emphasis on diverse transformations of carbonyl intermediates.

Main Results:

Demonstration of effective methods for accessing valuable products from alcohols.
Highlighting the use of alcohols as alkylating agents with water as the sole byproduct.
Showcasing a variety of metal and biocatalysts enabling these transformations.

Conclusions:

Borrowing hydrogen chemistry offers a versatile and efficient route for alcohol functionalization.
The review aims to increase the adoption of this technique across scientific disciplines.
Further development and application of borrowing hydrogen reactions are anticipated.