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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.

Lewis Acids and Bases

Lewis Acids and Bases

This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...

Lewis Acids and Bases

Lewis Acids and Bases

In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...

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.

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 Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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Related Experiment Video

Updated: Nov 2, 2025

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

Defunctionalisation catalysed by boron Lewis acids.

Huaquan Fang¹, Martin Oestreich¹

¹Institut für Chemie, Technische Universität Berlin Strasse des 17. Juni 115 10623 Berlin Germany martin.oestreich@tu-berlin.de.

Chemical Science

|June 7, 2021

Summary

Boron Lewis acid catalysis offers a sustainable alternative for defunctionalisation reactions, cleaving carbon-heteroatom bonds. This approach activates silicon-hydride bonds, enabling selective reduction processes like deoxygenation and dehalogenation.

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Last Updated: Nov 2, 2025

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

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Published on: February 20, 2020

Area of Science:

Organic Synthesis
Catalysis
Green Chemistry

Background:

Selective defunctionalisation is crucial for creating valuable organic intermediates.
Transition-metal catalysis faces limitations in industrial applications due to cost, toxicity, and non-renewability.
Boron Lewis acid catalysis presents a promising alternative for carbon-heteroatom bond cleavage.

Purpose of the Study:

To explore boron Lewis acid catalysis for selective defunctionalisation reactions.
To highlight the activation of silicon-hydride bonds by boron Lewis acids.
To summarize various defunctionalisation reactions catalyzed by boron Lewis acids.

Main Methods:

Utilisation of the strong boron Lewis acid B(C6F5)3 to activate Si-H bonds via η1 coordination.
Tuning of borane catalyst properties (electronic and structural) for chemoselectivity.
Employing various hydride sources in conjunction with the boron catalyst.

Main Results:

B(C6F5)3 activates Si-H bonds, forming a key Lewis adduct intermediate.
The catalytic system enables diverse reduction processes, including deoxygenation, decarbonylation, desulfurisation, deamination, and dehalogenation.
High chemoselectivity is achievable by modifying the catalyst and hydride source.

Conclusions:

Boron Lewis acid catalysis provides an efficient and selective method for defunctionalisation.
This approach offers a sustainable and industrially viable alternative to transition-metal catalysis.
The activation of Si-H bonds by boron Lewis acids is a versatile strategy for organic synthesis.