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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.

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...

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...

Exceptions to the Octet Rule

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NMR Spectroscopy of Benzene Derivatives

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Updated: Jun 7, 2025

Assessment of Boron Doped Diamond Electrode Quality and Application to In Situ Modification of Local pH by Water Electrolysis

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Published on: January 6, 2016

BODIPY Compounds Substituted on Boron.

Marko Bogomolec¹, Mladena Glavaš¹, Irena Škorić²

¹Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička Cesta 54, 10 000 Zagreb, Croatia.

Molecules (Basel, Switzerland)

|November 9, 2024

Summary

This review explores modifying the boron atom in BODIPY dyes, offering new ways to tune photophysical properties and solubility. These advancements pave the way for novel photocleavable protective groups with potential drug delivery applications.

Keywords:

BODIPY compounds boron chemistry fluorescent dyes photocages

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Published on: November 30, 2022

Area of Science:

Organic Chemistry
Photochemistry
Materials Science

Background:

BODIPY dyes are versatile organic dyes with tunable spectral and photophysical properties.
Structural modifications, primarily at the meso-position or pyrrole rings, are common.
Substitution of fluorine atoms and modification of the boron atom remain largely unexplored areas.

Purpose of the Study:

To review methods for preparing 4-substituted BODIPY compounds.
To highlight key reactions involving the boron atom of BODIPY dyes.
To emphasize the potential of underdeveloped photochemical reactions of the boron atom.

Main Methods:

Review of synthetic methodologies for boron modification in BODIPY dyes.
Discussion of reactions promoted by Lewis acids (e.g., AlCl3, BCl3) and bases (alkoxides, organometallic reagents).
Analysis of B-F bond cleavage and substitution with B-C, B-N, or B-O bonds.

Main Results:

Established methods for preparing 4-substituted BODIPY compounds are presented.
Key reactions enabling B-F bond substitution at the boron center are detailed.
The potential for tuning photophysical properties, solubility, and aggregation via boron modification is demonstrated.

Conclusions:

Modification of the boron atom offers a distinct route to tune BODIPY dye properties without altering spectral characteristics.
Photochemical reactions at the boron atom are a promising, yet underdeveloped, area.
These findings support the development of novel BODIPY-based photocleavable protective groups for bio-medicinal and photo-pharmacological applications, including drug delivery.