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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...

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.

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.

Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.

Acid Halides to Alcohols: LiAlH4 Reduction

Acid Halides to Alcohols: LiAlH₄ Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...

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Related Experiment Video

Updated: Mar 11, 2026

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

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

Published on: November 9, 2019

CO₂ Reduction by Lanthanum Borohydride Complexes and Hydroboration Reactivity.

Disha Bhattacharjee¹, Harsh P Singh¹, Hugh J Sanderson¹

¹LCM, CNRS, École Polytechnique, Institut Polytechnique de Paris, Route de Saclay, 91120 Palaiseau, France.

Inorganic Chemistry

|March 9, 2026

Summary

Lanthanide borohydride complexes react with carbon dioxide (CO2) to form formate complexes. These complexes can be further transformed into valuable borylated methanol products using hydroborane reagents.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Area of Science:

Organometallic Chemistry
Rare-Earth Chemistry
Catalysis

Background:

Lanthanide borohydride complexes are key precursors for molecular lanthanide compounds.
The reactivity of the borohydride ligand in these complexes remains underexplored.

Purpose of the Study:

To investigate the reactivity of lanthanide borohydride complexes with carbon dioxide (CO2).
To explore the potential of these complexes in CO2 transformation and valorization.

Main Methods:

Reaction of [La(Cp^ttt)2(BH4)] with CO2.
Analysis of reaction products using 1H DOSY NMR spectroscopy.
Investigation of subsequent reactions with hydroborane reagents (BH3, HBPin, H(9-BBN)).

Main Results:

Formation of a formate complex from the reaction of [La(Cp^ttt)2(BH4)] with CO2, existing as a monomer-dimer equilibrium.
Characterization of the formate complex using 1H DOSY NMR.
Synthesis of borylated methanol and lanthanide boroxide complexes via reaction with hydroborane reagents.

Conclusions:

Lanthanide borohydride complexes exhibit novel reactivity towards CO2.
These complexes show potential as precatalysts for CO2 hydroboration, enabling CO2 valorization.