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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.
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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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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sp3d and sp3d 2 Hybridization
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Phosphine→Borane-Functionalized Pyrenes and Anthracenes.

Arnaud Le Gac1, Sonia Mallet-Ladeira2, Julien Roger3

  • 1University of Toulouse: Universite de Toulouse, LHFA, FRANCE.

Angewandte Chemie (International Ed. in English)
|February 26, 2025
PubMed
Summary
This summary is machine-generated.

Phosphine→borane Lewis pairs functionalize polycyclic aromatic hydrocarbons (PAHs), significantly altering their optical and electrochemical properties. This P,B-functionalization reduces energy gaps and enhances fluorescence in pyrene and anthracene derivatives.

Keywords:
Anthracene * Fluorescence * Lewis Pair * Polycyclic Aromatic Hydrocarbons * Pyrene

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are extensively studied for their unique electronic and photophysical properties.
  • Functionalization of PAHs, particularly through borylative fusion with N→B Lewis pairs, offers a route to tune these properties by extending the π-system.
  • Previous research focused on N→B Lewis pairs, prompting exploration into other Lewis pairs for PAH modification.

Purpose of the Study:

  • To investigate the impact of phosphine→borane (P→B) Lewis pair functionalization on polycyclic aromatic hydrocarbons (PAHs).
  • To explore how P→B interactions influence the electronic, optical, and electrochemical properties of pyrene and anthracene derivatives.
  • To determine the role of the number and position of P→B units on these modified PAHs.

Main Methods:

  • Synthesis of novel PAHs functionalized with phosphine→borane Lewis pairs.
  • Investigation of pyrene and anthracene derivatives featuring P→B units.
  • Spectroscopic and electrochemical analyses to evaluate optical and electronic properties.

Main Results:

  • P→B functionalization significantly impacts optical and electrochemical properties without extending the π-system.
  • Functionalized PAHs exhibit reduced Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) gaps.
  • Enhanced fluorescence properties were observed in the P,B-functionalized PAHs.
  • The number and placement of P→B units critically influence the observed property changes.

Conclusions:

  • Phosphine→borane Lewis pair functionalization is a viable strategy to modulate PAH properties.
  • Geometric enforcement of P→B interactions, rather than π-system extension, drives significant changes in electronic and optical behavior.
  • The study highlights the potential of P,B-functionalized PAHs for applications requiring tailored photophysical and electrochemical characteristics.