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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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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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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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C-S-Selective Stille-Coupling Enables Stereodefined Alkene Synthesis.

Jing Jing1, Ying Hu1, Zhenfeng Tian1

  • 1Key Laboratory of Organic Synthesis of Jiangsu Province, MOE Key Laboratory of Geriatric Diseases and Immunology, Suzhou Key Laboratory of Pathogen Bioscience and Anti-infective Medicine, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 215123, Suzhou, China.

Angewandte Chemie (International Ed. in English)
|July 30, 2024
PubMed
Summary

This study introduces a palladium-catalyzed Stille cross-coupling reaction for synthesizing stereodefined alkenes. The method achieves high C-S selectivity, enabling efficient alkene construction for drug discovery applications.

Keywords:
Stille couplingalkenylationchemoselectivitystereoselectivitythianthrenium salts

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Developing selective cross-coupling reactions is crucial for complex molecule synthesis.
  • Controlling site- and chemoselectivity in Stille couplings remains a challenge, especially with diverse functional groups.

Purpose of the Study:

  • To develop a highly C-S-selective Stille cross-coupling reaction.
  • To provide an efficient route to stereodefined tri- and tetrasubstituted alkenes.
  • To demonstrate the utility of the method in drug discovery.

Main Methods:

  • Palladium-catalyzed Stille cross-coupling between aryl thianthrenium salts and alkenyl stannanes.
  • Utilizing C-H thianthrenation and C-S alkenylation for selectivity control.
  • Employing poly(pseudo)halogenated arenes in the cross-coupling.

Main Results:

  • Achieved high C-S selectivity over C-I, C-Br, C-Cl, and C-OTf bonds.
  • Synthesized stereodefined tri- and tetrasubstituted alkenes stereoretentively.
  • Demonstrated selective C-X functionalization for sequential and multiple cross-couplings.

Conclusions:

  • The developed protocol offers an expedient access to valuable alkene motifs.
  • The method exhibits broad functional group tolerance and selectivity.
  • The protocol is applicable for modular installation of alkene motifs in pharmaceutical synthesis and drug discovery.