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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is...
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A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors.

Francesca Giulia Nacca1,2, Bonifacio Monti1, Eder João Lenardão3

  • 1Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences University of Perugia Via del Liceo 1, 06123 Perugia, Italy.

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Summary

This study details seleno-Michael reactions using zinc-selenolates generated in situ. The efficient biphasic reducing system demonstrated broad substrate scope, with potential for recycling the reducing agent.

Keywords:
conjugate additionnucleophilic additionreductionseleniumseleno-Michael reactionzinc

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Area of Science:

  • Organic Chemistry
  • Organoselenium Chemistry

Background:

  • Seleno-Michael reactions are valuable for forming carbon-selenium bonds.
  • Efficient methods for generating and utilizing zinc-selenolates are crucial for synthetic applications.

Purpose of the Study:

  • To investigate seleno-Michael type reactions using in situ generated zinc-selenolates.
  • To explore the scope and limitations of these reactions with various electron-deficient alkenes.
  • To assess the recyclability of the reducing system.

Main Methods:

  • In situ generation of zinc-selenolates from diphenyl diselenide, 1,2-bis(3-phenylpropyl)diselenide, and protected selenocystine.
  • Utilizing an efficient biphasic zinc/hydrochloric acid (Zn/HCl) reducing system.
  • Reaction optimization and substrate scope evaluation with diverse alkenes.

Main Results:

  • Successful seleno-Michael addition to acyclic α,β-unsaturated ketones, aldehydes, esters, amides, and acids.
  • Accommodation of alkyl substituents at the β-position of alkenes.
  • Efficient Se-addition to cyclic enones, yielding adducts in moderate to good yields.
  • Incompatibility observed with vinyl sulfones, α,β-unsaturated nitriles, and chalcones.
  • Demonstrated recyclability of the Zn/HCl reducing system over seven cycles with 91% conversion yield.

Conclusions:

  • The developed method provides an efficient route for seleno-Michael additions.
  • The biphasic Zn/HCl system is effective for generating zinc-selenolates and is recyclable, enhancing sustainability.
  • The reaction exhibits good functional group tolerance for a range of electron-deficient alkenes.