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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Quantitative Reactivity Models for Oxidative Addition to L2Pd(0): Additional Substrate Classes, Solvents, and

Jingru Lu1, Holly Celuszak1, Irina Paci1

  • 1Department of Chemistry, University of Victoria, 3800 Finnerty Rd., Victoria, BC V8P 5C2, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 19, 2024
PubMed
Summary

We developed a quantitative model to predict reaction rates for palladium-catalyzed oxidative addition. This model aids in designing chemical syntheses and understanding reaction mechanisms.

Keywords:
Cross-couplingOrganopalladiumOxidative additionSolvent effectsStructure-reactivity relationships

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Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics
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Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Chemical Kinetics

Background:

  • Quantitative structure-reactivity models are crucial for predicting reaction outcomes and guiding synthetic strategies.
  • Palladium-catalyzed oxidative addition is a fundamental transformation in organic synthesis.

Purpose of the Study:

  • To expand and refine a multivariate linear regression (MLR) model for predicting the rates of (hetero)aryl (pseudo)halide oxidative addition to L2Pd(0) complexes.
  • To investigate the influence of substrate class and solvent on oxidative addition rates.
  • To explore the mechanistic basis of predictive descriptors and identify reaction outliers.

Main Methods:

  • Development and application of multivariate linear regression (MLR) modeling.
  • Inclusion of additional substrate classes (aryl chlorides, iodides) and solvents (THF, toluene, THF/DMF).
  • Analysis of molecular electrostatic potential (ESP) descriptors and bond strength metrics (IBSI, BDE).

Main Results:

  • A unified MLR model was established, showing minimal solvent effects across diverse substrates.
  • A simplified four-descriptor model was developed, effective for aryl halides but not 2-halopyridines.
  • 2-pyridyl triflate was identified as a mechanistic outlier, proceeding via nucleophilic displacement oxidative addition.

Conclusions:

  • The refined MLR model provides a robust tool for predicting oxidative addition rates.
  • The study highlights the importance of descriptor selection for model accuracy and mechanistic interpretation.
  • Understanding C-X bond strength metrics (IBSI vs. BDE) is key to comprehending oxidative addition reactivity.