Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Bronsted 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 Bronsted acid catalyst in the reaction.

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

Ruggieri, S;
2021-01-01

Abstract

Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Bronsted 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 Bronsted acid catalyst in the reaction.
2021
Sulfur Ylides
Chemodivergency
Chromenes
Dihydrobenzofurans
Organocatalysis
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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/11562/1097631
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 7
social impact