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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 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.

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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Related Experiment Video

Updated: Jan 7, 2026

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations

Published on: October 12, 2019

Semiconducting Borophene Realized via Hydrogenation-Driven Structural Reconstruction.

Meiling Xu¹, Zitong Wu², Jingyan Chen¹

¹Jiangsu Key Laboratory of Extreme Multi-Field Materials Physics, School of Physics and Electronic Engineering, Jiangsu Normal University, Xuzhou, 221116, China.

Angewandte Chemie (International Ed. in English)

|December 27, 2025

Summary

Hydrogenation stabilizes borophene, creating semiconducting properties essential for nanoelectronics. Researchers synthesized air-stable, semi-hydrogenated borophene (α′-B8H4), paving the way for advanced electronic devices.

Keywords:

Chemical vapor deposition First‐principles calculations Semiconducting borophene Semi‐hydrogenation Structural reconstruction

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Last Updated: Jan 7, 2026

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations

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Published on: October 12, 2019

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Area of Science:

Materials Science
Condensed Matter Physics
Nanotechnology

Background:

Borophene's potential in nanoelectronics is limited by instability and lack of semiconducting properties.
Hydrogenation is a promising strategy to overcome these limitations.
Identifying stable, semiconducting hydrogenated borophene phases is challenging due to diverse adsorption patterns.

Purpose of the Study:

To systematically search for and identify stable, semiconducting hydrogenated borophene phases.
To synthesize and characterize a predicted semiconducting borophene phase.
To elucidate the mechanism behind hydrogenation-induced semiconducting behavior in borophene.

Main Methods:

High-throughput computational searches for hydrogen adsorption configurations on α′-borophene.
Chemical vapor deposition synthesis of predicted semi-hydrogenated borophene.
Extensive structural characterization using experimental techniques.
Complementary computational simulations to validate structural and electronic properties.

Main Results:

Systematic searches identified semi-hydrogenated configurations as promising semiconducting candidates.
Successful synthesis of air-stable, semi-hydrogenated borophene (α′-B8H4).
Experimental and computational evidence confirmed the formation of a stable semiconducting phase.
Discovered hydrogenation-induced structural reconstruction and B-H bonding, leading to band gap opening via orbital hybridization.

Conclusions:

Air-stable, semiconducting borophene (α′-B8H4) has been identified and synthesized.
The study elucidates the mechanism for achieving semiconducting behavior in hydrogenated borophene.
This work establishes borophene as a viable material for next-generation electronic and optoelectronic applications.