Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Brønsted acid catalysis has been poorly explored. Herein, we report a new catalyst- and substrate- dependent chemodivergent reaction between stabilised sulfur ylides and salicylaldehydes, leading to the (suprising) formation of 2H-chromenes or dihydrobenzofurans products. Particular attention was set on the unusual mechanisms involved. Two unique reaction routes including two ylide units in the reactions are proposed. These pathways were validated by performing a selectivity switch in some cases, enabled by the modulation of the nucleophilicity of the sulfur ylide, and by the loading of the Brønsted acid catalyst in the reaction.

Catalyst- and Substrate-Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes / Giorgiana D. Bisag; Ruggieri S.; Fochi M.; Bernardi L.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 363:12(2021), pp. 3053-3059. [10.1002/adsc.202100124]

Catalyst- and Substrate-Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes

Giorgiana D. Bisag;Ruggieri S.;Fochi M.;Bernardi L.
2021

Abstract

Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Brønsted acid catalysis has been poorly explored. Herein, we report a new catalyst- and substrate- dependent chemodivergent reaction between stabilised sulfur ylides and salicylaldehydes, leading to the (suprising) formation of 2H-chromenes or dihydrobenzofurans products. Particular attention was set on the unusual mechanisms involved. Two unique reaction routes including two ylide units in the reactions are proposed. These pathways were validated by performing a selectivity switch in some cases, enabled by the modulation of the nucleophilicity of the sulfur ylide, and by the loading of the Brønsted acid catalyst in the reaction.
2021
Catalyst- and Substrate-Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes / Giorgiana D. Bisag; Ruggieri S.; Fochi M.; Bernardi L.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 363:12(2021), pp. 3053-3059. [10.1002/adsc.202100124]
Giorgiana D. Bisag; Ruggieri S.; Fochi M.; Bernardi L.
File in questo prodotto:
File Dimensione Formato  
adsc.202100124.pdf

accesso aperto

Tipo: Versione (PDF) editoriale
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione (CCBY)
Dimensione 5 MB
Formato Adobe PDF
5 MB Adobe PDF Visualizza/Apri
adsc202100124-sup-0001-misc_information.pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per accesso libero gratuito
Dimensione 3.81 MB
Formato Adobe PDF
3.81 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/852113
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 6
social impact