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Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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.

Esters to Alcohols: Hydride Reductions

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...

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.

Oxidation-Reduction Reactions

Oxidation-Reduction Reactions

Oxidation–Reduction Reactions

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...

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Related Experiment Video

Updated: May 26, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Borohydride Oxidation as Counter Reaction in Reductive Electrosynthesis.

Julius Kuzmin¹, Malin Lill¹, Guillermo Ahumada¹

¹Department of Chemistry, KTH Royal Institute of Technology, 10044, Stockholm, Sweden.

Angewandte Chemie (International Ed. in English)

|February 24, 2025

Summary

Anodic borohydride oxidation offers a sustainable alternative to sacrificial anodes in electroreduction. This method generates hydrogen gas using inert electrodes, improving the efficiency of reductive organic transformations.

Keywords:

Organic electrosynthesis counter reaction reductive transformations tetrabutylammonium borohydride

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Area of Science:

Electrochemistry
Organic Synthesis
Sustainable Chemistry

Background:

Efficient counter electrode reactions are crucial for electrochemical transformations.
Electrooxidative processes commonly use cathodic proton reduction to H2 as a benchmark.
Net reductive transformations often rely on sacrificial anodes, leading to material waste.

Purpose of the Study:

To explore anodic borohydride oxidation as a replacement for sacrificial anodes in electroreduction.
To demonstrate the viability of this method for various electroreductive organic transformations.
To establish an efficient and sustainable counter reaction for net reductive processes.

Main Methods:

Investigated anodic oxidation of borohydride as a counter reaction.
Utilized inert carbon-based electrode materials.
Applied the method to a range of electroreductive organic transformations.

Main Results:

Anodic borohydride oxidation effectively replaces sacrificial anodes.
The process generates hydrogen gas (H2) using inert electrodes.
This method is suitable for diverse electroreductive organic synthesis.

Conclusions:

Anodic borohydride oxidation is a promising, sustainable counter reaction for electroreduction.
It offers an inverse process to cathodic proton reduction, minimizing waste.
This approach enhances the efficiency and environmental friendliness of electroorganic synthesis.