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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.

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...

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.

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Exceptions to the Octet Rule

Exceptions to the Octet Rule

Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:

Covalent Bonding and Lewis Structures

Covalent Bonding and Lewis Structures

Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual attraction of atoms for a “shared” pair of electrons.

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Related Experiment Video

Updated: Oct 17, 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

First-Row d-Block Element-Catalyzed Carbon-Boron Bond Formation and Related Processes.

Shubhankar Kumar Bose¹, Lujia Mao², Laura Kuehn³

¹Centre for Nano and Material Sciences (CNMS), Jain University, Jain Global Campus, Bangalore-562112, India.

Chemical Reviews

|October 7, 2021

Summary

This summary is machine-generated.

First-row d-block transition metals are emerging as cost-effective catalysts for forming carbon-boron bonds. This review highlights their growing importance in organoboron chemistry and synthetic applications.

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Last Updated: Oct 17, 2025

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

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Published on: October 3, 2014

Area of Science:

Synthetic Organic Chemistry
Organometallic Chemistry

Background:

Organoboron reagents are crucial in organic synthesis, enabling diverse chemical transformations.
Stereocontrolled formation of carbon-X bonds from carbon-boron bonds is vital across multiple scientific fields.

Purpose of the Study:

To review the current advancements in using first-row d-block transition metal catalysts.
To highlight the shift from precious metal catalysts to more accessible alternatives in organoboron chemistry.

Main Methods:

Literature review of recent studies on first-row d-block transition metal catalysis.
Analysis of catalytic methods for carbon-boron bond formation.

Main Results:

First-row d-block transition metals are increasingly utilized as catalysts for carbon-boron bond formation.
These catalysts offer a more economical alternative to traditional precious metal catalysts.
Significant progress has been made in developing new synthetic methodologies.

Conclusions:

First-row d-block transition metal catalysis is a rapidly developing area in organoboron chemistry.
This catalytic approach expands the toolkit for synthesizing complex molecules.
The use of these catalysts has broad implications for medicinal chemistry, agrochemistry, and materials science.