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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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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...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.1K
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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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Preparation of Alcohols via Addition Reactions02:15

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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...
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Reversible Boron-Insertion into Aromatic C-C Bonds.

Kaito Kuroki1, Tatsuyoshi Ito1, Jun Takaya1

  • 1Department of Chemistry, School of Science, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

Angewandte Chemie (International Ed. in English)
|September 21, 2023
PubMed
Summary

Researchers achieved novel boron-doped bicyclic systems from triarylboranes via photo-promoted reactions. These compounds exhibit reversible photochemical and thermal transformations, offering new pathways in boron chemistry.

Keywords:
BoronC−C Bond CleavageElectrocyclizationFrustrated Lewis PairsPhotoreaction

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Area of Science:

  • Organometallic Chemistry
  • Photochemistry
  • Organic Synthesis

Background:

  • Triarylboranes with ortho-phosphino substituents are known as ambiphilic phosphine-boranes.
  • Skeletal rearrangement reactions offer pathways to novel molecular architectures.

Purpose of the Study:

  • To investigate the photo-promoted skeletal rearrangement of ortho-phosphino substituted triarylboranes.
  • To synthesize and characterize novel boron-doped bicyclic compounds.
  • To explore the photochemical and thermal reversibility of the formed systems.

Main Methods:

  • Photo-promoted skeletal rearrangement reaction.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for characterization.
  • X-ray crystallography for structural determination.
  • Experimental and theoretical studies (computational chemistry).

Main Results:

  • Formation of borabicyclo[3.2.0]heptadiene derivatives through boron insertion into aromatic C-C bonds.
  • Full characterization of the synthesized borabicyclo[3.2.0]heptadiene derivatives.
  • Demonstration of photochemical and thermal interconversion between triarylboranes and boron-doped bicyclic systems.
  • Identification of a highly strained trans-borepin intermediate via sequential electrocyclic reactions and E/Z-isomerization.

Conclusions:

  • The study successfully synthesized novel boron-doped bicyclic systems via a photo-promoted reaction.
  • The synthesized compounds exhibit unique reversible photochemical and thermal properties.
  • The reaction mechanism involves sequential electrocyclic reactions and a strained intermediate, providing insights into boron chemistry.