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Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Radical Chain-Growth Polymerization: Overview01:10

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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.3K
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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Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

1.5K
In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Visualizing Lignification Dynamics in Plants with Click Chemistry: Dual Labeling is BLISS!
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Taming the radical cation intermediate enabled one-step access to structurally diverse lignans.

Jia-Chen Xiang1,2, Cédric Fung1, Qian Wang1

  • 1Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, 1015, Lausanne, Switzerland.

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This study presents a novel, short synthetic route to diverse lignans using biomass-derived monolignols. The method employs blue LED irradiation and readily available reagents to efficiently produce various lignan structures.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Biomass Valorization

Background:

  • Lignans are structurally diverse natural products biosynthetically derived from coniferyl alcohol.
  • Efficient synthesis of lignans is crucial for their study and application.

Purpose of the Study:

  • To develop a divergent and short synthetic strategy for lignans from biomass-derived monolignols.
  • To achieve selective synthesis of various lignan scaffolds and analogues.

Main Methods:

  • Blue LED irradiation of dicinnamyl ether derivatives in dichloromethane.
  • Utilizing copper(II) trifluoroacetate (Cu(TFA)2) or diphenyl disulfide (PhSSPh) as catalysts.
  • Employing alcohols and Fukuzumi's salt to control reaction pathways.

Main Results:

  • Achieved C7-alkoxylated aryltetralin cyclic ethers using Cu(TFA)2 and 2.0 equiv alcohol.
  • Synthesized C7,C7'-dialkoxylated dibenzyltetrahydrofurans by increasing alcohol concentration.
  • Produced C7-monoalkoxylated dibenzyltetrahydrofurans using PhSSPh.
  • Demonstrated access to aza-, thia-, and carba-analogues of lignans.
  • Completed concise total syntheses of aglacins A, E, F, brassilignan, and dehydrodimethylconidendrin.

Conclusions:

  • A versatile and efficient synthetic methodology for lignans and their analogues has been established.
  • The developed method allows for controlled, divergent synthesis from readily available starting materials.
  • This approach facilitates the concise total synthesis of complex lignan natural products.