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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.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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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...
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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...
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This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.
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Facile Preparation and Photoactivation of Prodrug-Dye Nanoassemblies
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Substitution at boron in BODIPYs.

Rosinah Liandrah Gapare1, Alison Thompson1

  • 1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, NS, B3H 4R2, Canada. Alison.Thompson@dal.ca.

Chemical Communications (Cambridge, England)
|June 20, 2022
PubMed
Summary

This study explores the chemistry of boron atoms in 4,4-disubstituted-4-bora-3a,4a-diaza-s-indacenes (BODIPYs). Researchers highlight synthetic routes and boron

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Recent advancements in synthetic chemistry have produced diverse 4,4-disubstituted-4-bora-3a,4a-diaza-s-indacenes (BODIPYs).
  • Substituents at various positions (meso, pyrrolic, boron) significantly impact BODIPY photophysical properties and applications.
  • The dipyrrolic skeleton of BODIPYs offers potential for broad utility.

Purpose of the Study:

  • To provide an overview of the chemistry occurring at the boron atom within BODIPY molecules.
  • To highlight the evolution of research on boron-substituted BODIPYs from initial synthetic curiosities to versatile compounds.
  • To discuss strategies for facile substitution at the boron atom.

Main Methods:

  • Summarization of preparative routes for BODIPY synthesis via boron complexation with dipyrrinato ligands.

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  • Discussion of the protective role of boron in dipyrrin structures.
  • Exploration of synthetic strategies for modifying the boron atom.

    • Main Results:

    • Established synthetic pathways for BODIPY construction.
    • Demonstrated the crucial role of the boron atom in stabilizing the dipyrrin core.
    • Identified methods for achieving controlled substitution at the boron site.

    Conclusions:

    • The chemistry at the boron atom is central to the synthesis and functionalization of BODIPY dyes.
    • Understanding boron's role expands the applicability of the dipyrrolic skeleton.
    • Facile boron substitution opens avenues for tailored BODIPY derivatives with tunable properties.