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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Thermal Sigmatropic Reactions: Overview01:16

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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
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Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

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The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
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Solvents01:12

Solvents

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A solvent is a substance, most often a liquid, that can dissolve other substances. Here, the substance being dissolved is called a solute. When a solvent and a solute combine, they form a solution - a homogenous mixture of both the solvent and the solute. Water is a universal biological solvent. Its polar structure allows it to dissolve many other polar compounds. The ability of water to dissolve is governed by a balance between water molecules binding to each other and binding to the solute.
A...
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Enthalpy of Solution02:39

Enthalpy of Solution

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There are two criteria that favor, but do not guarantee, the spontaneous formation of a solution:
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Bayesian Optimization of Solvent-Free Thermal Amidation via Reactive Extrusion.

Matthieu Lavayssiere1, Xavier Bantreil1,2, Frédéric Lamaty1

  • 1IBMM, Univ Montpellier, CNRS, ENSCM, Montpellier, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 26, 2026
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Summary

This study presents a green method for synthesizing amides using an extruder, eliminating solvents and catalysts. A Bayesian optimization approach efficiently guided the process for high yields and sustainability.

Keywords:
APIsBayesian optimizationamidemechanochemistryreactive extrusion

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Area of Science:

  • Green Chemistry
  • Organic Synthesis
  • Process Chemistry

Background:

  • Traditional amide synthesis often requires harsh conditions, coupling agents, and organic solvents, posing environmental and economic challenges.
  • Developing sustainable and efficient synthetic routes for amides, crucial in pharmaceuticals and materials, is a significant goal in organic chemistry.

Purpose of the Study:

  • To report a novel solvent-free, catalyst-free, and additive-free thermo-mechanochemical synthesis of amides using an extruder.
  • To develop and apply a Bayesian optimization (BO) strategy for optimizing reaction parameters and enhancing sustainability.
  • To demonstrate the versatility of the method for synthesizing various amides, including bioactive compounds and active pharmaceutical ingredients (APIs).

Main Methods:

  • Solvent-free synthesis of amides via thermo-mechanochemical activation in a twin-screw extruder.
  • Application of Bayesian optimization (BO) with active and soft constraints to optimize temperature, reaction time, and reactant ratios.
  • Isolation and purification of amides through direct extrusion, extraction, or crystallization.

Main Results:

  • Achieved high yields in amide synthesis using a straightforward and sustainable extruder-based methodology.
  • Demonstrated broad substrate scope, successfully synthesizing diverse amides, including macamides and moclobemide.
  • Optimized conditions allowed for product isolation with minimal purification, and notably, moclobemide was synthesized and isolated without organic solvents at a larger scale.

Conclusions:

  • The developed thermo-mechanochemical extrusion method offers a highly efficient, sustainable, and adaptable route for amide synthesis.
  • Bayesian optimization effectively guided the process towards high conversion and improved sustainability metrics.
  • This solvent-free approach represents a significant advancement in green chemistry for the production of valuable amide compounds.