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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
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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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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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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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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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Methane Beryllation Catalyzed by a Base Metal Complex.

Josef T Boronski1, Agamemnon E Crumpton2, Job J C Struijs2

  • 1Molecular Sciences Research Hub, Department of Chemistry, Imperial College London, 82 Wood Lane, White City, London W12 0BZ, U.K.

Journal of the American Chemical Society
|March 11, 2025
PubMed
Summary
This summary is machine-generated.

Researchers achieved the challenging catalytic functionalization of methane using novel beryllation reactions. Photochemical conditions and specific manganese or rhenium catalysts enabled the conversion of strong C-H bonds in methane and benzene.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Methane functionalization is difficult due to its nonpolar nature and strong C-H bonds.
  • Homogeneous catalysis offers potential pathways but faces significant hurdles.

Purpose of the Study:

  • To develop a novel method for the catalytic functionalization of methane and benzene C-H bonds.
  • To investigate the role of beryllation in C-H bond activation.

Main Methods:

  • Photochemical reactions utilizing catalytic amounts (10 mol %) of CpMn(CO)3 or Cp*Re(CO)3.
  • Isolation and characterization of reaction intermediates, including trans-bis(berilyl)-manganese and -rhenium complexes.
  • Quantum chemical calculations to elucidate reaction mechanisms.

Main Results:

  • Successful conversion of methane and benzene C-H bonds to C-Be and H-Be bonds using CpBeBeCp under photochemical conditions.
  • Isolation of key manganese and rhenium beryllation intermediates.
  • Identification of beryllyl ligands' σ-donating and Lewis acidic properties as crucial for methane functionalization.

Conclusions:

  • CpMn(CO)3 and Cp*Re(CO)3 catalyze the beryllation of methane and benzene under photochemical conditions.
  • The unique electronic properties of beryllyl ligands facilitate C-H bond activation.
  • This study presents a new strategy for the homogeneous catalytic functionalization of inert hydrocarbons.