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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.

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...

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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Related Experiment Video

Updated: Aug 23, 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

Substrate-Mediated Borophane Polymorphs through Hydrogenation of Two-Dimensional Boron Sheets.

Yuchong Kang¹, Xiaoyun Ma¹, Jing Fu¹

¹Ningxia Key Laboratory of Photovoltaic Materials, School of Materials and New Energy, Ningxia University, Yinchuan, Ningxia750021, P.R. China.

The Journal of Physical Chemistry Letters

|October 27, 2022

Summary

Hydrogenation stabilizes two-dimensional boron (borophene) into borophane. Optimal adsorption sites depend on borophene structure and metal substrates, offering insights for material stabilization.

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

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Area of Science:

Materials Science
Condensed Matter Physics
Surface Science

Background:

Borophene, a 2D boron allotrope, exhibits unique electronic and mechanical properties.
Its structural flexibility allows for numerous polymorphs, but stability is a concern.

Purpose of the Study:

Investigate precise hydrogen adsorption structures on borophene (forming borophane).
Elucidate the underlying mechanisms governing hydrogenation.
Determine optimal configurations for freestanding and supported borophenes.

Main Methods:

First-principles calculations were employed.
Analyzed freestanding borophene polymorphs.
Studied borophene on various metallic substrates.

Main Results:

Energetically favorable hydrogen adsorption sites on freestanding borophene are polymorph-dependent.
Hydrogenation configurations are significantly modulated by metal substrates due to orbital overlap.
Identified specific B p and H s orbital interactions influencing adsorption.

Conclusions:

Provided deep insights into borophene hydrogenation mechanisms.
Demonstrated that hydrogen adsorption site and concentration engineering can stabilize 2D boron polymorphs.
Findings facilitate the rational design of stable borophene-based materials.