Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2024

Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins

Patrick Wagner
  • Fonction : Auteur
Mihaela Gulea
Nicolas Girard
  • Fonction : Auteur
  • PersonId : 1108714

Résumé

The rhodium-catalyzed hydroformylation of alkynyl sulfides at 40 °C under 5 bars of syngas is described. The method gives access to α-sulfenyl acroleins with α/β regioselectivities up to 89/11 and is applicable to alkyl or aryl substituted substrates. It is effective even on more complex substrates, such as cysteine and cholesterol derivatives. To demonstrate the synthetic potential of the obtained products, (Z)-3-cyclohexyl-2-methylsulfenyl acrolein was selected as an example and its sulfur atom selectively oxidized to the corresponding sulfoxide or sulfone. Acid-promoted (Z) to (E) isomerization of the double bond occurred during oxidation. The three obtained sulfenyl-, sulfinyl-, and sulfonyl-functionalized acroleins have been then used as dienophiles to access cyclohexene carbaldehydes.

Domaines

Catalyse
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Origine : Publication financée par une institution
Licence : CC BY - Paternité

Dates et versions

hal-04568170 , version 1 (07-05-2024)

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Citer

Patrick Wagner, Mihaela Gulea, Nicolas Girard. Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins. Advanced Synthesis and Catalysis, 2024, 366 (6), pp.1298-1305. ⟨10.1002/adsc.202301349⟩. ⟨hal-04568170⟩
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